4-Oxo-4-phenylmethoxy-2-(phenylmethoxycarbonylamino)butanoic acid

Base Information

• Chemical Name: 4-Oxo-4-phenylmethoxy-2-(phenylmethoxycarbonylamino)butanoic acid
• CAS No.: 3479-47-8
• Molecular Formula: C19H19NO6
• Molecular Weight: 357.363
• Hs Code.: 29242990
• NSC Number: 163521,118536
• ChEMBL ID: CHEMBL1609505
• Mol file: 3479-47-8.mol

Synonyms:29880-21-5;Z-D,L-Asp(OBzl)-OH;Z-Dl-Asp(Obzl)-OH;4-oxo-4-phenylmethoxy-2-(phenylmethoxycarbonylamino)butanoic acid;MLS000776577;4-(Benzyloxy)-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid;SMR000371826;4-(BENZYLOXY)-2-{[(BENZYLOXY)CARBONYL]AMINO}-4-OXOBUTANOIC ACID;C19H19NO6;Z-DL-aspartic acid b-benzyl ester;NSC163521;Z-DL-Aspartic acid beta-benzyl ester;Opera_ID_644;SCHEMBL2912589;CHEMBL1609505;VUKCNAATVIWRTF-UHFFFAOYSA-N;HMS2691M11;Z-L-aspartic acid beta-benzyl ester;NSC118536;NSC-118536;NSC-163521;O-Benzyl-N-carbobenzyloxy-aspartic acid;NCGC00245976-01;BS-27747;N-carbobenzyloxy-.beta.-benzyl-l-aspartate;FT-0601296;FT-0689482;N-CBZ-L-ASPARTIC ACID B-BENZYL ESTER;A822403;Z56753807;4-(benzyloxy)-2-(benzyloxycarbonylamino)-4-oxobutanoic acid;4-(benzyloxy)-2(((benzyloxy)carbonyl)amino)-4-oxobutanoic acid;4-(Benzyloxy)-2-(((benzyloxy)carbonyl)amino)-4-oxobutanoicacid;Aspartic acid,N-[(phenylmethoxy)carbonyl]-,4-(phenylmethyl)ester

Chemical Property of 4-Oxo-4-phenylmethoxy-2-(phenylmethoxycarbonylamino)butanoic acid

Chemical Property:

• Appearance/Colour: White to off-white powder
• Vapor Pressure: 1.21E-14mmHg at 25°C
• Melting Point: 105-107 °C
• Refractive Index: 1.581
• Boiling Point: 587.4 °C at 760 mmHg
• PKA: 3.63±0.23(Predicted)
• Flash Point: 309.1 °C
• PSA: 101.93000
• Density: 1.293 g/cm³
• LogP: 2.89040
• Storage Temp.: Store at RT.
• Water Solubility.: Insoluble in water.
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 357.12123733
• Heavy Atom Count: 26
• Complexity: 469

Purity/Quality:

99% ^*data from raw suppliers

Z-L-aspartic acid-beta-benzyl ester ^*data from reagent suppliers

Safty Information:

• Statements: 50
• Safety Statements: 61

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC=C(C=C1)COC(=O)CC(C(=O)O)NC(=O)OCC2=CC=CC=C2
• Uses: It is widely used as a pharmaceutical intermediate and in food industry.

Technology Process of 4-Oxo-4-phenylmethoxy-2-(phenylmethoxycarbonylamino)butanoic acid

There total 9 articles about 4-Oxo-4-phenylmethoxy-2-(phenylmethoxycarbonylamino)butanoic acid 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: 100.0%

di(phenylmethyl) (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate (5241-60-1) → Z-Asp(OBzl)-OH (3479-47-8)

Guidance literature:

With 4-methyl-morpholine; In water; acetonitrile; at 30 ℃; for 96h; under 7500600 Torr;

DOI:10.1021/jo00020a001

Reference yield: 98.0%

(S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid (2177-63-1,25248-99-1) + benzyl chloroformate (501-53-1,94274-21-2) → Z-Asp(OBzl)-OH (3479-47-8)

Guidance literature:

With sodium hydrogencarbonate; In tetrahydrofuran; water; at 20 ℃; for 1h;

DOI:10.1021/jo201429w

Reference yield: 58.0%

3-hydroxymethylpyridin (100-55-0) + Isopropenyl chloroformate (57933-83-2) + N-Cbz-L-Asp (1152-61-0) → Z-Asp(OBzl)-OH (3479-47-8) + Z-Asp-OBn (4779-31-1)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 1h; Yield given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(00)95388-7

upstream raw materials:

di(phenylmethyl) (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate

(S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid

benzyl chloroformate

3-hydroxymethylpyridin

Downstream raw materials:

α-L-Asp-ε-L-Lys

N-(O-benzyl-N-benzyloxycarbonyl-L-α-aspartyl)-L-leucine benzyl ester

(S)-2-amino-4-(benzyloxy)-4-oxobutanoic acid

N-benzyloxycarbonyl-L-asparagine

Refernces

• 1、 Yoshida, Masanori,Narita, Mao,Hara, Shoji. "Asymmetric michael addition of malonates to enones catalyzed by a primary Β-amino acid and its lithium salt". experimental part. p. 8513 - 8517. Retrieved 2011/12/03.
• 2、 Burtin, Guillaume,Corringer, Pierre-Jean,Hitchcock, Peter B.,Young, Douglas W.. "Stereoselective synthesis of β-substituted aspartic acids via tetrahydro-1,3-oxazin-6-ones". . p. 4275 - 4278. Retrieved 2007/10/03.