tert-butyl (3S)-3-amino-3-phenylpropanoate

Base Information

• Chemical Name: tert-butyl (3S)-3-amino-3-phenylpropanoate
• CAS No.: 120686-18-2
• Molecular Formula: C13H19NO2
• Molecular Weight: 221.299
• Hs Code.: 29224999
• Nikkaji Number: J830.220K
• Mol file: 120686-18-2.mol

Synonyms:120686-18-2;tert-butyl (3S)-3-amino-3-phenylpropanoate;(S)-tert-Butyl 3-amino-3-phenylpropanoate;MFCD00798310;TERT-BUTYL-(3S)-3-AMINO-3-PHENYLPROPANOATE;(S)-tert-Butyl3-amino-3-phenylpropanoate;SCHEMBL1573827;TYYCBAISLMKLMT-NSHDSACASA-N;AKOS015894819;AS-48214;t-Butyl (3S)-3-amino-3-phenylpropanoate;tert-Butyl (S)-3-amino-3-phenylpropanoate;CS-0134777;tert-Butyl (3S)-3-amino-3-phenyl-propanoate;F19790;EN300-6512257;[(S)-alpha-(2-Oxo-2-tert-butoxyethyl)benzyl]amine;tert-Butyl (3S)-3-amino-3-phenylpropanoate, AldrichCPR;Benzenepropanoic acid,b-amino-,1,1-dimethylethyl ester,(bs)-

Chemical Property of tert-butyl (3S)-3-amino-3-phenylpropanoate

Chemical Property:

• Appearance/Colour: clear colorless to light brown
• Vapor Pressure: 0.000354mmHg at 25°C
• Refractive Index: 1.496-1.498
• Boiling Point: 318.7 °C at 760 mmHg
• PKA: 7?+-.0.10(Predicted)
• Flash Point: 170.6 °C
• PSA: 52.32000
• Density: 1.04 g/cm³
• LogP: 3.11850
• Storage Temp.: 2-8°C
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 221.141578849
• Heavy Atom Count: 16
• Complexity: 227

Purity/Quality:

96% 1H NMR ^*data from raw suppliers

Benzenepropanoicacid,?-amino-,1,1-dimethylethylester,(?S)- 96% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C,Xn
• Statements: 34-52-22
• Safety Statements: 45-36/37/39-26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CC(C1=CC=CC=C1)N
• Isomeric SMILES: CC(C)(C)OC(=O)C[C@@H](C1=CC=CC=C1)N

Technology Process of tert-butyl (3S)-3-amino-3-phenylpropanoate

There total 27 articles about tert-butyl (3S)-3-amino-3-phenylpropanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 91.0%

tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate (151133-00-5) → (S)-3-amino-3-phenylpropionic acid tert-butyl ester (120686-18-2)

Guidance literature:

With hydrogen; acetic acid; palladium dihydroxide; In methanol; water; at 20 ℃; for 24h; under 760.051 Torr;

DOI:10.1016/j.tetasy.2007.06.008

Reference yield: 76.0%

C31H43NO3 (1037302-71-8) → 2-methoxy-d-bornyl aldehyde (1037303-05-1) + (S)-3-amino-3-phenylpropionic acid tert-butyl ester (120686-18-2)

Guidance literature:

C₃₁H₄₃NO₃; With N-iodo-succinimide; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

With water; sodium hydrogencarbonate; sodium thiosulfate; In dichloromethane; at 20 ℃; Inert atmosphere;

DOI:10.1021/ol8007793

Reference yield: 14.0%

tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate (151133-00-5) → tert-butyl 3-phenylpropanoate (16537-10-3) + (S)-3-amino-3-phenylpropionic acid tert-butyl ester (120686-18-2) + tert-butyl (R)-3-amino-3-phenylpropionate (161671-34-7) + tert-butyl (3S,αR)-3-phenyl-3-N-(α-methylbenzyl)aminopropanoate (213467-19-7)

Guidance literature:

With hydrogen; palladium dihydroxide; In ethanol; for 72h; under 2850.23 Torr; Title compound not separated from byproducts;

DOI:10.1002/1522-2675(200201)85:1<161::AID-HLCA161>3.0.CO;2-L

upstream raw materials:

tert-butyl (3S)-N-(benzyloxycarbonyl)-3-amino-3-phenylpropanoate

tert-butyl (3S,αR)-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-phenylpropanoate

tert-butyl (E)-[(R)-p-tolylsulfinyl]cinnamate

tert-butyl diethylphosphonoacetate

Downstream raw materials:

(E)-3-((S)-2-tert-Butoxycarbonyl-1-phenyl-ethylcarbamoyl)-4-phenyl-but-3-enoic acid ethyl ester

(S)-3-amino-3-phenylpropanoic acid

(S)-3-((2E,4E)-Hexa-2,4-dienoylamino)-3-phenyl-propionic acid tert-butyl ester

(S)-3-((2E,4E,6E)-Octa-2,4,6-trienoylamino)-3-phenyl-propionic acid tert-butyl ester

Refernces

• 1、 M?enp??, Harri,Kanerva, Liisa T.,Liljeblad, Arto. "Acylation of β-Amino Esters and Hydrolysis of β-Amido Esters: Candida antarctica Lipase A as a Chemoselective Deprotection Catalyst". . p. 1226 - 1232. Retrieved 2016/04/05.
• 2、 Davies, Stephen G.,Lee, James A.,Roberts, Paul M.,Thomson, James E.,Yin, Jingda. "Double asymmetric induction as a mechanistic probe: The doubly diastereoselective conjugate addition of enantiopure lithium amides to enantiopure α,β-unsaturated esters and enantiopure α,β-unsaturated hydroxamates". experimental part. p. 6382 - 6403. Retrieved 2011/09/19.