(3R)-3-benzyloxycarbonylamino-3-methyl-1-((2RS)-2-methoxycarbonyl-3-phthalimidopropyl)pyrrolidine-2-thione

Base Information

• Chemical Name: (3R)-3-benzyloxycarbonylamino-3-methyl-1-((2RS)-2-methoxycarbonyl-3-phthalimidopropyl)pyrrolidine-2-thione
• CAS No.: 951172-74-0
• Molecular Formula: C₂₆H₂₇N₃O₆S
• Molecular Weight: 509.583
• Mol file: 951172-74-0.mol

Synonyms:(3R)-3-benzyloxycarbonylamino-3-methyl-1-((2RS)-2-methoxycarbonyl-3-phthalimidopropyl)pyrrolidine-2-thione

Chemical Property of (3R)-3-benzyloxycarbonylamino-3-methyl-1-((2RS)-2-methoxycarbonyl-3-phthalimidopropyl)pyrrolidine-2-thione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-3-benzyloxycarbonylamino-3-methyl-1-((2RS)-2-methoxycarbonyl-3-phthalimidopropyl)pyrrolidine-2-thione

There total 9 articles about (3R)-3-benzyloxycarbonylamino-3-methyl-1-((2RS)-2-methoxycarbonyl-3-phthalimidopropyl)pyrrolidine-2-thione 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: 56.0%

(3R)-3-benzyloxycarbonylamino-3-methyl-1-((2RS)-2-methoxycarbonyl-3-phthalimidopropyl)pyrrolidin-2-one → (3R)-3-benzyloxycarbonylamino-3-methyl-1-((2RS)-2-methoxycarbonyl-3-phthalimidopropyl)pyrrolidine-2-thione (951172-74-0) + C26H27N3O5S2

Guidance literature:

With Lawessons reagent; In toluene; for 1.5h; Heating;

DOI:10.1021/jo071074x

Reference yield:

methyl 3-amino-2-(phthalimidomethyl)propanoate hydrobromide → (3R)-3-benzyloxycarbonylamino-3-methyl-1-((2RS)-2-methoxycarbonyl-3-phthalimidopropyl)pyrrolidine-2-thione (951172-74-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 15.5 g / sodium cyanoborohydride; acetic acid / methanol / 72 h / 20 °C / pH 6

2: 56 percent / Lawesson's reagent / toluene / 1.5 h / Heating

With Lawessons reagent; sodium cyanoborohydride; acetic acid; In methanol; toluene;

DOI:10.1021/jo071074x

Reference yield:

methyl 3-benzylamino-2-(phthalimidomethyl)propanoate (951172-71-7) → (3R)-3-benzyloxycarbonylamino-3-methyl-1-((2RS)-2-methoxycarbonyl-3-phthalimidopropyl)pyrrolidine-2-thione (951172-74-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / bromine / H₂O; CH₂Cl₂ / 4.5 h

2: 15.5 g / sodium cyanoborohydride; acetic acid / methanol / 72 h / 20 °C / pH 6

3: 56 percent / Lawesson's reagent / toluene / 1.5 h / Heating

With Lawessons reagent; bromine; sodium cyanoborohydride; acetic acid; In methanol; dichloromethane; water; toluene;

DOI:10.1021/jo071074x

upstream raw materials:

methyl 3-benzylamino-2-(phthalimidomethyl)propanoate

(2S,4S)-3-benzyloxycarbonyl-4-methyl-2-phenyl-4-(prop-2-enyl)oxazolidin-5-one

(2S,4S)-3-benzyloxycarbonyl-4-methyl-4-(2-oxoethyl)-2-phenyloxazolidin-5-one

methyl 2-(bromomethyl)propenoate

Downstream raw materials:

(3R)-3-benzyloxycarbonylamino-3-methyl-1-((2RS)-3-amino-2-methoxycarbonylpropyl)pyrrolidine-2-thione

(3S,7S)-7-benzyloxycarbonylamino-3-methoxycarbonyl-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene

(3S,7S)-7-benzyloxycarbonylamino-3-carboxy-3,7-dimethyl-1,5-diazabicyclo[4.3.0]non-5-ene