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G. Yu et al.
PAPER
C-Benzo[1,3]dioxol-5-ylmethylamine Hydrogen Chloride (3)
1H NMR (500 MHz, CD3OD): δ = 4.2 (s, 2 H), 6.1 (s, 2 H), 7.0 (s,
1 H), 7.1 (s, 1H).
13C NMR (125 MHz, CD3OD): δ = 42.0, 104.0, 111.0, 111.5, 124.8,
13C NMR (125 MHz, CD3OD): δ = 52.5, 54.3, 127.8, 130.3, 132.3,
133.6, 168.4.
HRMS: m/z calcd for C7H8ClNO2S [M + H]+: 206.0043; found:
206.0039.
127.7, 148.9, 150.9.
2-(S)-Amino-3-(5-chlorothiophen-2-yl)propionic Acid Methyl
Ester Hydrogen Chloride (11)
HRMS: m/z calcd for C8H8NO2Cl: 186.0321; found: 186.0316.
1H NMR (500 MHz, DMSO-d6): δ = 3.35 (q, 2 H), 3.75 (s, 3 H),
4.34 (t, 1 H), 6.88 (d, 1 H), 7.02 (d, 1 H), 8.67 (br s, 3 H).
Amino-(3-chloro-4-methoxyphenyl)acetic Acid Methyl Ester
Hydrogen Chloride (4)
1H NMR (500 MHz, CD3OD): δ = 3.8 (s, 3 H), 3.9 (s, 3 H), 5.2 (s,
1 H), 7.2 (s, 1 H), 7.4 (s, 1 H), 7.5 (s, 1 H).
13C NMR (125 MHz, DMSO-d6): δ = 29.9, 52.7, 52.8, 126.9, 127.1,
128.3, 135.2, 168.8.
13C NMR (125 MHz, CD3OD): δ = 49.0, 56.6, 56.9, 114.0, 124.2,
HRMS: m/z calcd for C8H10ClNO2S [M + H]+: 220.0199; found:
126.6, 129.3, 130.8, 157.7, 170.5.
220.0191.
HRMS: m/z calcd for C10H12NO3Cl: 230.0584; found: 230.0588.
2-(R)-Amino-3-(5-chlorothiophen-2-yl)propionic Acid Methyl
Ester Hydrogen Chloride (12)
5-Chloro-2-methoxyphenylmethylamine Hydrogen Chloride
(5)
1H NMR (500 MHz, DMSO-d6): δ = 3.33 (q, 2 H), 3.74 (s, 3 H),
4.32 (t, 1 H), 6.87 (d, 1 H), 7.01 (d, 1 H), 8.68 (br s, 3 H).
1H NMR (500 MHz, DMSO-d6): δ = 3.8 (s, 3 H), 3.9 (m, 2 H), 7.1
(d, 1 H), 7.4 (d, 1 H), 7.5 (s, 1 H).
13C NMR (125 MHz, DMSO-d6): δ = 29.9, 52.7, 52.8, 126.9, 127.1,
128.3, 135.2, 168.8.
HRMS: m/z calcd for C8H10ClNO2S [M + H]+: 220.0199; found:
13C NMR (125 MHz, DMSO-d6): δ = 37.5, 56.7, 113.4, 124.5,
124.6, 130.2, 130.5, 156.7.
220.0201.
HRMS: m/z for C8H10NClO: 172.0529; found: 172.0532.
2-(S)-Amino-3-(3-chloro-4-hydroxyphenyl)propionic Acid Me-
thyl Ester Hydrogen Chloride (13)
4-Chloro-3-methoxyphenylmethylamine Hydrogen Chloride
and 2-Chloro-3-methoxybenzylamine Hydrogen Chloride (6a
and 6b)
1H NMR (500 MHz, DMSO-d6): δ = 3.02 (d, 2 H), 3.70 (s, 3 H),
4.26 (t, 1 H), 6.95 (q, 2 H), 7.22 (s, 1 H), 8.51 (br s, 3 H).
1H NMR (500 MHz, DMSO-d6): δ = 3.8 (s, 3 H), 4.2 (s, 2 H), 7.0
(d, 1 H), 7.1 (s, 1 H), 7.4 (d, 1 H).
13C NMR (125 MHz, DMSO-d6): δ = 34.5, 52.6, 53.2, 116.8, 119.5,
126.0, 129.0, 130.7, 152.4, 169.3.
HRMS: m/z calcd for C10H12ClNO3 [M + H]+: 230.0584; found:
13C NMR (125 MHz, DMSO-d6): δ = 39.4, 55.7, 115.7, 116.1,
123.63, 130.1, 132.6, 158.1.
230.0582.
HRMS: m/z for C8H10NClO: 172.0529; found: 172.0528.
2-(R)-Amino-3-(3-chloro-4-hydroxyphenyl)propionic Acid Me-
thyl Ester Hydrogen Chloride (14)
(5-Chlorothiophen-2-yl)methylamine Hydrogen Chloride (7)
1H NMR (500 MHz, DMSO-d6): δ = 4.18 (s, 2 H), 7.10 (d, 1 H),
7.13 (d, 1 H), 8.42(br s, 3 H).
13C NMR (125 MHz, DMSO-d6): δ = 36.0, 126.7, 130.0, 129.4,
1H NMR (500 MHz, DMSO-d6): δ = 3.02 (d, 2 H), 3.71 (s, 3 H),
4.25 (t, 1 H), 6.97 (q, 2 H), 7.22 (s, 1 H), 8.50 (br s, 3 H).
13C NMR (125 MHz, DMSO-d6) : δ = 34.5, 52.6, 53.3, 115.5, 116.8,
126.0, 129.0, 130.7, 152.5, 169.3.
HRMS: m/z calcd for C10H12ClNO3 [M + H]+: 230.0584; found:
230.0586.
134.7.
HRMS: m/z calcd for C5H6ClNS [M + H + CH3CN]+: 189.0253;
found: 189.0256.
2-(5-Chlorothiophen-2-yl)ethylamine Hydrogen Chloride (8)
1H NMR (500 MHz, DMSO-d6): δ = 3.04 (s, 4 H), 6.87 (d, 1 H),
7.01 (d, 1 H), 8.10(br s, 3 H).
13C NMR (125 MHz, DMSO-d6): δ = 28.4, 122.4, 127.0, 127.8,
2-(S)-Amino-3-(3-chloro-4-methoxyphenyl)propionic Acid Me-
thyl Ester Hydrogen Chloride (15)
1H NMR (500 MHz, DMSO-d6): δ = 3.13 (d, 2 H), 3.68 (s, 3 H),
3.83 (s, 3 H), 4.23 (t, 1 H), 7.09 (d, 1 H), 7.17 (q, 1 H), 7.35 (d, 1
H), 8.80 (br s, 3 H).
132.6, 139.7.
HRMS: m/z calcd for C6H8ClNS [M + H]+: 162.0144; found:
162.0140.
13C NMR (125 MHz, DMSO-d6): δ = 34.5, 52.5, 53.1, 56.1, 112.8,
120.9, 127.8, 129.4, 130.8, 153.7, 169.2.
HRMS: m/z calcd for C11H14ClNO3 [M + H]+: 244.0740; found:
244.0743.
(R)-Amino-(5-chlorothiophen-2-yl)acetic Acid Methyl Ester
Hydrogen Chloride (9)
1H NMR (500 MHz, CD3OD): δ = 3.85 (s, 3 H), 5.51 (s, 1 H), 7.01
(d, 1 H), 7.12 (d, 1 H).
2-(R)-Amino-3-(3-chloro-4-methoxyphenyl)propionic Acid Me-
thyl Ester Hydrogen Chloride (16)
13C NMR (125 MHz, CD3OD): δ = 52.5, 54.2, 127.6, 130.1, 132.0,
133.5, 168.3.
HRMS: m/z calcd for C7H8ClNO2S [M + H]+: 206.0043; found:
1H NMR (500 MHz, DMSO-d6): δ = 3.08 (d, 2 H), 3.71 (s, 3 H),
3.84 (s, 3 H), 4.30(t, 1 H), 7.12 (d, 1 H), 7.16 (q, 1 H), 7.34 (d, 1 H),
8.52 (br s, 3 H).
13C NMR (125 MHz, DMSO-d6): δ = 34.0, 52.6, 53.1, 56.1, 112.8,
206.0035.
120.8, 127.8, 129.4, 130.8, 153.7, 169.2.
HRMS: m/z calcd for C11H14ClNO3 [M + H]+: 244.0740; found:
244.0742.
(S)-Amino-(5-chlorothiophen-2-yl)acetic Acid Methyl Ester
Hydrogen Chloride (10)
1H NMR (500 MHz, CD3OD): δ = 3.85 (s, 3 H), 5.51 (s, 1 H), 7.01
(d, 1 H), 7.13(d, 1 H).
Synthesis 2003, No. 3, 403–407 ISSN 0039-7881 © Thieme Stuttgart · New York