(S)-2-tert-Butoxycarbonylamino-2-[(R)-5-isopropyl-4-oxo-5-(2-oxo-ethyl)-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-tert-Butoxycarbonylamino-2-[(R)-5-isopropyl-4-oxo-5-(2-oxo-ethyl)-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester
• CAS No.: 145452-10-4
• Molecular Formula: C₂₄H₃₂N₂O₆
• Molecular Weight: 444.528
• Mol file: 145452-10-4.mol

Synonyms:(S)-2-tert-Butoxycarbonylamino-2-[(R)-5-isopropyl-4-oxo-5-(2-oxo-ethyl)-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

Chemical Property of (S)-2-tert-Butoxycarbonylamino-2-[(R)-5-isopropyl-4-oxo-5-(2-oxo-ethyl)-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-tert-Butoxycarbonylamino-2-[(R)-5-isopropyl-4-oxo-5-(2-oxo-ethyl)-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

There total 27 articles about (S)-2-tert-Butoxycarbonylamino-2-[(R)-5-isopropyl-4-oxo-5-(2-oxo-ethyl)-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl 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: 100.0%

(S)-2-tert-Butoxycarbonylamino-2-[(R)-5-(2,3-dihydroxy-3-methyl-butyl)-5-isopropyl-4-oxo-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester → (S)-2-tert-Butoxycarbonylamino-2-[(R)-5-isopropyl-4-oxo-5-(2-oxo-ethyl)-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester (145452-10-4)

Guidance literature:

With sodium periodate; In tetrahydrofuran; water; for 1h; Ambient temperature;

DOI:10.1021/ja00101a017

Reference yield: 85.0%

2-tert-butoxycarbonylamino-2-[5-(2-hydroxy-ethyl)-5-isopropyl-4-oxo-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester (288404-51-3) → (S)-2-tert-Butoxycarbonylamino-2-[(R)-5-isopropyl-4-oxo-5-(2-oxo-ethyl)-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester (145452-10-4)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.333333h;

DOI:10.1021/ol0059293

Reference yield:

(R)-2-Amino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester (145452-08-0) → (S)-2-tert-Butoxycarbonylamino-2-[(R)-5-isopropyl-4-oxo-5-(2-oxo-ethyl)-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester (145452-10-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / i-Pr₂NEt / tetrahydrofuran / 4 h / 20 °C

2: 95 percent / O₃; PPh₃ / -78 °C

3: 78 percent / NaBH₃CN; aq. HCl / methanol / 3 h / 20 °C

4: 83 percent / H₂ / Pd(C) / ethanol / 1 h

5: toluene

6: 77 percent / KHMDS; 18-crown-6 / tetrahydrofuran / 3 h / 20 °C

7: 85 percent / (COCl)2; DMSO; DBU / CH₂Cl₂ / 0.33 h / 20 °C

With hydrogenchloride; oxalyl dichloride; 18-crown-6 ether; hydrogen; potassium hexamethylsilazane; sodium cyanoborohydride; ozone; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; toluene; 1: benzyloxycarbonylation / 2: Oxidation / 3: Reduction / 4: Hydrogenation / 5: Condensation / 6: Ring cleavage / 7: Swern oxidation;

DOI:10.1021/ol0059293

upstream raw materials:

2-tert-butoxycarbonylamino-2-[5-(2-hydroxy-ethyl)-5-isopropyl-4-oxo-4,5-dihydro-1H-pyrrol-3-yl]-3-phenyl-propionic acid methyl ester

(R)-2-Amino-2-isopropyl-5-methyl-hex-4-enoic acid methyl ester

(R)-3-Amino-3-isopropyl-dihydro-furan-2-one

((R)-3-Isopropyl-2-oxo-tetrahydro-furan-3-yl)-carbamic acid benzyl ester

Downstream raw materials:

(S)-2-tert-Butoxycarbonylamino-2-[(2S,5'S)-5'-isobutyl-2-isopropyl-5'-(3-methyl-but-2-enyl)-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-4-yl]-3-phenyl-propionic acid methyl ester

(S)-2-tert-Butoxycarbonylamino-2-[(2S,5'S,5''S)-5',5''-diisobutyl-2-isopropyl-5''-(3-methyl-but-2-enyl)-3,4',4''-trioxo-2,3,4',5',4'',5''-hexahydro-1H,1'H,1''H-[2,3';5',3'']terpyrrol-4-yl]-3-phenyl-propionic acid methyl ester

2-tert-butoxycarbonylamino-2-[5''-(2-hydroxy-ethyl)-5',5''-diisobutyl-2-isopropyl-3,4',4''-trioxo-2,3,4',5',4'',5''-hexahydro-1H,1'H,1''H-[2,3';5',3'']terpyrrol-4-yl]-3-phenyl-propionic acid methyl ester

(S)-2-tert-Butoxycarbonylamino-2-[(2S,5'S)-5'-(2-hydroxy-ethyl)-5'-isobutyl-2-isopropyl-3,4'-dioxo-2,3,4',5'-tetrahydro-1H,1'H-[2,3']bipyrrolyl-4-yl]-3-phenyl-propionic acid methyl ester