(3S)-N-tert-butyloxycarbonyl-5-hydroxy-3-phenyl-L-proline methyl ester

Base Information

• Chemical Name: (3S)-N-tert-butyloxycarbonyl-5-hydroxy-3-phenyl-L-proline methyl ester
• CAS No.: 366498-32-0
• Molecular Formula: C₁₇H₂₃NO₅
• Molecular Weight: 321.373
• Mol file: 366498-32-0.mol

Synonyms:(3S)-N-tert-butyloxycarbonyl-5-hydroxy-3-phenyl-L-proline methyl ester

Chemical Property of (3S)-N-tert-butyloxycarbonyl-5-hydroxy-3-phenyl-L-proline methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S)-N-tert-butyloxycarbonyl-5-hydroxy-3-phenyl-L-proline methyl ester

There total 2 articles about (3S)-N-tert-butyloxycarbonyl-5-hydroxy-3-phenyl-L-proline 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: 70.0%

methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate (366498-31-9) → (3S)-N-tert-butyloxycarbonyl-5-hydroxy-3-phenyl-L-proline methyl ester (366498-32-0)

Guidance literature:

methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate; With boron trifluoride-tetrahydrofuran complex; In tetrahydrofuran; at 0 - 20 ℃;

With 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; at 0 - 20 ℃;

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/S0040-4020(01)00532-4

Reference yield:

Caesium; (2S,3S)-2-tert-butoxycarbonylamino-3-phenyl-pent-4-enoate → (3S)-N-tert-butyloxycarbonyl-5-hydroxy-3-phenyl-L-proline methyl ester (366498-32-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 2.7 g / dimethylformamide / 24 h

2.1: BF₃*THF / tetrahydrofuran / 0 - 20 °C

2.2: MCPBA / tetrahydrofuran / 0 - 20 °C

2.3: 70 percent / DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 20 °C

With boron trifluoride-tetrahydrofuran complex; In tetrahydrofuran; N,N-dimethyl-formamide; 2.3: Swern oxidation;

DOI:10.1016/S0040-4020(01)00532-4

Reference yield:

(3S)-N-tert-butyloxycarbonyl-5-hydroxy-3-phenyl-L-proline methyl ester (366498-32-0) → (3S,6S,8S,9S)-1,4-diaza-3-benzyl-9-carbomethoxy-8-phenyl-2-oxo bicyclo-[4,3,0]nonane

Guidance literature:

Multi-step reaction with 6 steps

1.1: 90 mg / PPTS / 24 h / 20 °C

2.1: CuBr*Me₂S / diethyl ether / 1 h / -40 °C

2.2: 92 percent / BF₃*Et₂O / diethyl ether / 0.25 h

3.1: aq. HCl / 0.5 h / 20 °C

4.1: 450 mg / N-ethylmorpholine / CH₂Cl₂ / 24 h

5.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

5.2: 90 percent / Me₂S / CH₂Cl₂ / -78 - 20 °C

6.1: 80 percent / H₂ / Pd/BaSO₄ / methanol / 24 h

With N-ethylmorpholine;; hydrogenchloride; copper(I) bromide dimethylsulfide complex; hydrogen; pyridinium p-toluenesulfonate; ozone; Pd-BaSO₄; In methanol; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4020(01)00532-4

upstream raw materials:

methyl (2S,3S)-2-[N-(tert-butyloxycarbonyl)amino]-3-phenyl-4-pentenoate

Downstream raw materials:

(3S)-N-tert-butyloxycarbonyl-5-methoxy-3-phenyl-L-proline methyl ester

(3S)-N-tert-butyloxycarbonyl-5-methoxy-3-phenyl-D-proline methyl ester

(3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(trans-1-propenyl)-L-proline methyl ester

(3S,5S)-N-tert-butyloxycarbonyl-3-phenyl-5-(2-methyl-1-propenyl)-L-proline methyl ester