(4S,2S)-4-Chloro-<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene

Base Information

• Chemical Name: (4S,2S)-4-Chloro-<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene
• CAS No.: 159750-06-8
• Molecular Formula: C₂₄H₂₇ClN₂O₅
• Molecular Weight: 458.942
• Mol file: 159750-06-8.mol

Synonyms:(4S,2S)-4-Chloro-<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene

Chemical Property of (4S,2S)-4-Chloro-<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,2S)-4-Chloro-<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene

There total 7 articles about (4S,2S)-4-Chloro-<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene 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: 90.0%

di-tert-butyl dicarbonate (24424-99-5) + (4S,2S)-4-Chloro-<2-azido-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene (159750-02-4) → (4S,2S)-4-Chloro-<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene (159750-06-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethyl acetate; for 3h; Ambient temperature;

DOI:10.1021/jo970508t

Reference yield:

3-(4-chlorophenyl)propanoic acid (2019-34-3) → (4S,2S)-4-Chloro-<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene (159750-06-8)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) 0 deg C, 45 min

2: n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) -78 deg C, 15 min and room temp., 10 h

3: 1.) KHMDS, 2.) trisyl azide / 1.) THF, toluene, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 min

4: H₂, 5 N HCl / 10percent Pd-C / tetrahydrofuran; methanol / 8 h / 760 Torr / Ambient temperature

5: K₂CO₃ / tetrahydrofuran; H₂O / Ambient temperature

With hydrogenchloride; n-butyllithium; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; potassium hexamethylsilazane; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo00088a009

Reference yield:

3-(4-chlorophenyl)prop-2-enoic acid (1615-02-7,940-62-5) → (4S,2S)-4-Chloro-<2-<<(1,1-dimethylethoxy)carbonyl>amino>-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene (159750-06-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / H₂ / 10percent Pd-C / tetrahydrofuran / 4 h / Ambient temperature

2: Et₃N / tetrahydrofuran / 1.) -78 deg C, 15 min, 2.) 0 deg C, 45 min

3: n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2.) -78 deg C, 15 min and room temp., 10 h

4: 1.) KHMDS, 2.) trisyl azide / 1.) THF, toluene, -78 deg C, 30 min, 2.) THF, -78 deg C, 2 min

5: H₂, 5 N HCl / 10percent Pd-C / tetrahydrofuran; methanol / 8 h / 760 Torr / Ambient temperature

6: K₂CO₃ / tetrahydrofuran; H₂O / Ambient temperature

With hydrogenchloride; n-butyllithium; 2,4,6-Triisopropylbenzenesulfonyl azide; hydrogen; potassium hexamethylsilazane; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; water;

DOI:10.1021/jo00088a009

upstream raw materials:

di-tert-butyl dicarbonate

(4S,2S)-4-Chloro-<2-azido-3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene

3-(4-chlorophenyl)propanoic acid

3-(4-chlorophenyl)prop-2-enoic acid

Downstream raw materials:

Boc-p-chloro-L-Phe-OH

(S)-3-<4-<2-Carboxy-2-<<(1,1-dimethylethoxy)carbonyl>amino>ethyl>phenoxy>-O-methyl-N--L-tyrosinyl>-L-tyrosine α-methyl ester

N-<(1,1-Dimethylethoxy)carbonyl>-4-chloro-L-phenylalanine 2-bromoethyl ester

(S)-3-<4-<2-<<(1,1-Dimethylethoxy)carbonyl>amino>-3-oxo-3-(2-bromoethoxy)propyl>phenoxy>-O-methyl-N--L-tyrosinyl>-L-tyrosine α-methyl ester