(S)-Benzyl (1-hydrazinyl-3-hydroxy-1-oxopropan-2-yl)carbamate

Base Information

• Chemical Name: (S)-Benzyl (1-hydrazinyl-3-hydroxy-1-oxopropan-2-yl)carbamate
• CAS No.: 26582-86-5
• Molecular Formula: C11H15 N3 O4
• Molecular Weight: 253.258
• Hs Code.: 2928000090
• European Community (EC) Number: 247-822-8
• DSSTox Substance ID: DTXSID40949429
• Nikkaji Number: J248.973B
• Wikidata: Q82927343
• Mol file: 26582-86-5.mol

Synonyms:26582-86-5;Z-SER-NHNH2;(S)-Benzyl (1-hydrazinyl-3-hydroxy-1-oxopropan-2-yl)carbamate;benzyl N-[(2S)-1-hydrazinyl-3-hydroxy-1-oxopropan-2-yl]carbamate;EINECS 247-822-8;N-((Benzyloxy)carbonyl)-L-serinohydrazide;Z-Ser-NHNH;N-[(benzyloxy)carbonyl]-L-serinohydrazide;SCHEMBL11124419;DTXSID40949429;WUDRJXCGIRLAEC-VIFPVBQESA-N;MFCD00153341;N-(Benzyloxycarbonyl)-L-serine hydrazide;F10817;L-Serine,N-[(phenylmethoxy)carbonyl]-,hydrazide;(S)-benzyl 1-hydrazinyl-3-hydroxy-1-oxopropan-2-ylcarbamate;2-{[(Benzyloxy)(hydroxy)methylidene]amino}-3-hydroxypropanehydrazonic acid

Chemical Property of (S)-Benzyl (1-hydrazinyl-3-hydroxy-1-oxopropan-2-yl)carbamate

Chemical Property:

• Melting Point: 181 °C
• Boiling Point: 561.0±50.0 °C(Predicted)
• PKA: 10.74±0.46(Predicted)
• PSA: 113.68000
• Density: 1.322±0.06 g/cm3(Predicted)
• LogP: 0.74570
• Storage Temp.: Store at RT.
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 253.10625597
• Heavy Atom Count: 18
• Complexity: 280

Purity/Quality:

99% ^*data from raw suppliers

Z-L-serine hydrazide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)NC(CO)C(=O)NN
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](CO)C(=O)NN

Technology Process of (S)-Benzyl (1-hydrazinyl-3-hydroxy-1-oxopropan-2-yl)carbamate

There total 5 articles about (S)-Benzyl (1-hydrazinyl-3-hydroxy-1-oxopropan-2-yl)carbamate 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: 86.0%

N-benzyloxycarbonyl-L-serine methyl ester (1676-81-9) → benzyl (1S)-2-hydrazino-1-(hydroxymethyl)-2-oxoethylcarbamate (26582-86-5)

Guidance literature:

With hydrazine hydrate; In methanol; at 20 ℃; for 12h; Inert atmosphere;

DOI:10.1039/d0cc02728f

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → benzyl (1S)-2-hydrazino-1-(hydroxymethyl)-2-oxoethylcarbamate (26582-86-5)

Guidance literature:

Multi-step reaction with 2 steps

1: KHCO₃; ethyl acetate

2: ethanol; hydrazine hydrate

With ethanol; potassium hydrogencarbonate; hydrazine hydrate; ethyl acetate;

Reference yield:

N-(benzyloxycarbonyl)-L-serine ethyl ester (23161-27-5,28270-55-5) → benzyl (1S)-2-hydrazino-1-(hydroxymethyl)-2-oxoethylcarbamate (26582-86-5)

Guidance literature:

With hydrazine; In ethanol; at 0 ℃; Reflux;

DOI:10.2174/138620711794474033

upstream raw materials:

N-benzyloxycarbonyl-L-serine methyl ester

benzyl chloroformate

N-(benzyloxycarbonyl)-L-serine ethyl ester

N-(benzyloxycarbonyl)-L-serine

Downstream raw materials:

N-(benzyloxycarbonyl)-L-seryl-L-aspartic diethyl ester

benzyl (1S)-2-[(2E)-2-(2,4-dihydroxybenzylidene)hydrazino]-1-(hydroxymethyl)-2-oxoethylcarbamate

benzyl (1S)-2-[(2E)-2-(3,4-dihydroxybenzylidene)hydrazino]-1-(hydroxymethyl)-2-oxoethylcarbamate

benzyl (1S)-1-(hydroxymethyl)-2-[(2E/Z)-2-(2-nitrobenzylidene)hydrazino]-2-oxoethylcarbamate

Refernces

• 1、 Nogueira, Thais C. M.,Pinheiro, Alessandra C.,Kaiser, Carlos R.,Wardell, James L.,Wardell, Solange M. S. V.,De Souza, Marcus V. N.. "A new synthesis of chiral oxazolidinones from the amino acid L-serine". . p. 626 - 631. Retrieved 2013/12/04.
• 2、 Woodard, Scott S.,Jerome, Kevin D.. "Combinatorial synthesis of 3,5-Dimethylene substituted 1,2,4-Triazoles". experimental part. p. 132 - 137. Retrieved 2012/04/18.