(S)-[1-[(Benzyloxy)carbamoyl]-2-hydroxyethyl]carbamic acid benzyl ester

Base Information

• Chemical Name: (S)-[1-[(Benzyloxy)carbamoyl]-2-hydroxyethyl]carbamic acid benzyl ester
• CAS No.: 26048-94-2
• Molecular Formula: C18H20N2O5
• Molecular Weight: 344.367
• DSSTox Substance ID: DTXSID10461062
• Mol file: 26048-94-2.mol

Synonyms:26048-94-2;(S)-[1-[(BENZYLOXY)CARBAMOYL]-2-HYDROXYETHYL]CARBAMIC ACID BENZYL ESTER;benzyl N-[(2S)-3-hydroxy-1-oxo-1-(phenylmethoxyamino)propan-2-yl]carbamate;Carbamic acid, N-[(1S)-1-(hydroxymethyl)-2-oxo-2-[(phenylmethoxy)amino]ethyl]-, phenylmethyl ester;DTXSID10461062;AKOS030242178;J-016238

Chemical Property of (S)-[1-[(Benzyloxy)carbamoyl]-2-hydroxyethyl]carbamic acid benzyl ester

Chemical Property:

• Melting Point: 127-129 °C(Solv: acetonitrile (75-05-8); ethyl ether (60-29-7))
• PKA: 10.54±0.46(Predicted)
• PSA: 103.87000
• Density: 1.268±0.06 g/cm3(Predicted)
• LogP: 2.56640
• Solubility.: Acetone, Chloroform, Dichloromethane
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 344.13722174
• Heavy Atom Count: 25
• Complexity: 406

Purity/Quality:

97% ^*data from raw suppliers

(S)-[1-[(Benzyloxy)carbamoyl]-2-hydroxyethyl]carbamicAcidBenzylEster ^*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)NOCC2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)COC(=O)N[C@@H](CO)C(=O)NOCC2=CC=CC=C2

Technology Process of (S)-[1-[(Benzyloxy)carbamoyl]-2-hydroxyethyl]carbamic acid benzyl ester

There total 7 articles about (S)-[1-[(Benzyloxy)carbamoyl]-2-hydroxyethyl]carbamic acid benzyl ester 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: 89.0%

N-benzyloxyamine (622-33-3) + N-(benzyloxycarbonyl)-L-serine (1145-80-8) → (S)-{2-[(phenylmethyloxy)amino]-1-(hydroxymethyl)-2-oxoethyl}carbamic acid phenylmethyl ester (26048-94-2)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In water; N,N-dimethyl-formamide; pH 4-5;

DOI:10.1021/ja00543a021

Reference yield: 83.5%

N-(N-benzyloxycarbonyl-O-dimethyl-t-butylsilyl-L-serinyl)-O-benzylhydroxylamine (104499-31-2) → (S)-{2-[(phenylmethyloxy)amino]-1-(hydroxymethyl)-2-oxoethyl}carbamic acid phenylmethyl ester (26048-94-2)

Guidance literature:

With tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; for 0.0833333h; Ambient temperature;

Reference yield:

Z-DL-serine (2768-56-1) → (S)-{2-[(phenylmethyloxy)amino]-1-(hydroxymethyl)-2-oxoethyl}carbamic acid phenylmethyl ester (26048-94-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 1) imidazole, 2) aq K₂CO₃ (10percent) / 1) DMF, 16 h, room temp., 2) MeOH, THF, 1 h, room temp.

2: 36.4 percent / WSC, DMAP / CH₂Cl₂ / 5 h / Ambient temperature

3: 66 percent / Et₃N / CH₂Cl₂ / 72 h / Ambient temperature

4: 83.5 percent / Bu₄NF, AcOH / tetrahydrofuran / 0.08 h / Ambient temperature

With 1H-imidazole; dmap; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In tetrahydrofuran; dichloromethane;

upstream raw materials:

N-benzyloxyamine

N-(benzyloxycarbonyl)-L-serine

N-(N-benzyloxycarbonyl-O-dimethyl-t-butylsilyl-L-serinyl)-O-benzylhydroxylamine

Z-DL-serine

Downstream raw materials:

(S)-[1-(phenylmethyloxy)-2-oxo-3-azetidinyl]carbamic acid phenylmethyl ester

(S)-3-[(phenylmethyloxy)amino]-N-[(phenylmethyloxy)carbonyl]alanine

(S)-3-[nitroso(phenylmethyloxy)amino]-N-[(phenylmethyloxy)carbonyl]alanine

(S)-3-[(phenylmethyloxy)amino]-N-[(phenylmethyloxy)carbonyl]alanine phenylmethyl ester