(S)-2-tert-butoxycarbonylamino-4-oxo-6-phenylhex-5-ynoic acid tert-butyl ester

Base Information

• Chemical Name: (S)-2-tert-butoxycarbonylamino-4-oxo-6-phenylhex-5-ynoic acid tert-butyl ester
• CAS No.: 197159-33-4
• Molecular Formula: C₂₁H₂₇NO₅
• Molecular Weight: 373.449
• Mol file: 197159-33-4.mol

Synonyms:(S)-2-tert-butoxycarbonylamino-4-oxo-6-phenylhex-5-ynoic acid tert-butyl ester

Chemical Property of (S)-2-tert-butoxycarbonylamino-4-oxo-6-phenylhex-5-ynoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-tert-butoxycarbonylamino-4-oxo-6-phenylhex-5-ynoic acid tert-butyl ester

There total 6 articles about (S)-2-tert-butoxycarbonylamino-4-oxo-6-phenylhex-5-ynoic acid tert-butyl 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-tert-butoxycarbonyl-L-aspartic acid α-tert-butyl ester β-N-methoxy-N-methylamide (122313-00-2) + phenylacetylene (536-74-3) → (S)-2-tert-butoxycarbonylamino-4-oxo-6-phenylhex-5-ynoic acid tert-butyl ester (197159-33-4)

Guidance literature:

phenylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h;

N-tert-butoxycarbonyl-L-aspartic acid α-tert-butyl ester β-N-methoxy-N-methylamide; In tetrahydrofuran; hexane; at -78 - -20 ℃; for 3h;

DOI:10.1002/ejoc.201300812

Reference yield: 62.0%

N-tert-butoxycarbonyl-L-aspartic acid α-tert-butyl ester β-N-methoxy-N-methylamide (122313-00-2) + lithium phenylacetylide (4440-01-1) → (S)-2-tert-butoxycarbonylamino-4-oxo-6-phenylhex-5-ynoic acid tert-butyl ester (197159-33-4)

Guidance literature:

In tetrahydrofuran; at -78 ℃;

DOI:10.1039/a704526c

Reference yield:

N-tert-butoxycarbonyl aspartic acid tert-butyl ester (34582-32-6) → (S)-2-tert-butoxycarbonylamino-4-oxo-6-phenylhex-5-ynoic acid tert-butyl ester (197159-33-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 4-methylmorpholine / tetrahydrofuran / -15 °C

2: Et₃N / tetrahydrofuran; dimethylformamide / 1.) -15 deg C, 30 min, 2.) r.t., 12 h

3: 1.) BuLi / 1.) THF, hexane, -78 deg C, 30 min, 2.) THF, hexane, -78 deg C, 30 min; -78 deg C to r.t., 2 h

With 4-methyl-morpholine; n-butyllithium; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1039/a806741d

upstream raw materials:

N-tert-butoxycarbonyl-L-aspartic acid α-tert-butyl ester β-N-methoxy-N-methylamide

lithium phenylacetylide

phenylacetylene

4-benzyl 1-t-butyl L-aspartate

Downstream raw materials:

(S)-α-tert-butoxycarbonylamino-β-(2-p-chlorophenyl-6-phenylpyrimidin-4-yl)propanoic acid α-tert-butyl ester

(S)-α-tert-butoxycarbonylamino-β-(2-methylthio-6-phenylpyrimidin-4-yl)propanoic acid α-tert-butyl ester

(S)-α-tert-butoxycarbonylamino-β-(2-methylsulfonyl-6-phenylpyrimidin-4-yl)propanoic acid α-tert-butyl ester

(S)-α-tert-butoxycarbonylamino-β-(2-amino-6-phenylpyrimidin-4-yl)propanoic acid α-tert-butyl ester