Methyl 4-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]benzoate

Base Information

• Chemical Name: Methyl 4-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]benzoate
• CAS No.: 160168-19-4
• Molecular Formula: C17H23 N O6
• Molecular Weight: 337.373
• DSSTox Substance ID: DTXSID70455588
• Nikkaji Number: J2.150.281B
• Wikidata: Q82277665
• Mol file: 160168-19-4.mol

Synonyms:160168-19-4;Methyl 4-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]benzoate;CTK4D0349;DTXSID70455588;GPYFDXNCJTUIKW-ZDUSSCGKSA-N;N-(tert-Butoxycarbonyl)-4-(methoxycarbonyl)-L-phenylalanine methyl ester

Chemical Property of Methyl 4-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]benzoate

Chemical Property:

• Melting Point: 82-83 °C(Solv: ethyl ether (60-29-7))
• Boiling Point: 464.0±45.0 °C(Predicted)
• PKA: 10.88±0.46(Predicted)
• PSA: 90.93000
• Density: 1.155±0.06 g/cm3(Predicted)
• LogP: 2.47290
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 337.15253745
• Heavy Atom Count: 24
• Complexity: 449

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC(CC1=CC=C(C=C1)C(=O)OC)C(=O)OC
• Isomeric SMILES: CC(C)(C)OC(=O)N[C@@H](CC1=CC=C(C=C1)C(=O)OC)C(=O)OC

Technology Process of Methyl 4-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]benzoate

There total 5 articles about Methyl 4-[(2S)-3-methoxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]benzoate 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%

4-methoxycarbonylphenyl bromide (619-42-1) + methyl (2R)-2-[(tert-butoxycarbonyl)amino]-3-bromopropionate (175844-11-8,402726-50-5) → 4-(carbomethoxy)-N-<(1,1-dimethylethoxy)carbonyl>-L-phenylalanine methyl ester (160168-19-4)

Guidance literature:

With 2,6-dimethylpyridine; (1,2-dimethoxyethane)dichloronickel(II); tris-(trimethylsilyl)silane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; 4,4'-di-tert-butyl-2,2'-bipyridine; In 1,2-dimethoxyethane; at 30 ℃; for 0.5h; Reagent/catalyst; Catalytic behavior; Sealed tube; Inert atmosphere; Irradiation; Flow reactor;

DOI:10.1021/acs.oprd.1c00208

Reference yield: 39.0%

methyl 4-iodobenzoate (619-44-3) + N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester (93267-04-0,170848-34-7,889670-02-4) → 4,4'-biphenyldicarboxylic acid dimethyl ester (792-74-5) + 4-(carbomethoxy)-N-<(1,1-dimethylethoxy)carbonyl>-L-phenylalanine methyl ester (160168-19-4)

Guidance literature:

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester; With iodine; zinc; In N,N-dimethyl-formamide; at 0 ℃; for 0.5h; Inert atmosphere;

methyl 4-iodobenzoate; With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; tris-(o-tolyl)phosphine; In N,N-dimethyl-formamide; at 60 ℃; for 5h; Inert atmosphere;

DOI:10.15227/orgsyn.081.0077

Reference yield:

4-methoxycarbonylphenyl bromide (619-42-1) + p-toluenesulfonic acid salt of L-serine (5042-77-3) → 4-(carbomethoxy)-N-<(1,1-dimethylethoxy)carbonyl>-L-phenylalanine methyl ester (160168-19-4)

Guidance literature:

With (1,2-dimethoxyethane)dichloronickel(II); tris-(trimethylsilyl)silane; [4,4′-bis(1,1-dimethylethyl)-2,2′-bipyridine-N1,N1′]bis{3,5-difluoro-2-[5-(trifluoromethyl)-2-pyridinyl-κN]phenyl-κC}iridium(III) hexafluorophosphate; tetrabutylammomium bromide; sodium carbonate; 4,4'-di-tert-butyl-2,2'-bipyridine; In 1,2-dimethoxyethane; at 30 ℃; for 4h; Sealed tube; Inert atmosphere; Irradiation;

DOI:10.1021/acs.oprd.1c00208

upstream raw materials:

methanol

carbon monoxide

methyl N-(tert-butoxycarbonyl)-O-[(trifluoromethyl)sulfonyl]-L-tyrosinate

methyl 4-iodobenzoate

Downstream raw materials:

4-<(cyclohexyloxy)carbonyl>-N-<(1,1-dimethylethoxy)carbonyl>-L-phenylalanine, cyclohexyl ester

4-(carboxy)-N-<(1,1-dimethylethoxy)carbonyl>-L-phenylalanine