(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

Base Information

• Chemical Name: (R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester
• CAS No.: 391213-74-4
• Molecular Formula: C₂₄H₂₈FN₃O₉
• Molecular Weight: 521.499

Synonyms:(R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

Chemical Property of (R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

There total 10 articles about (R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-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:

4-fluoro-3-nitrobenzaldehyde (42564-51-2) → (R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester (391213-74-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 99 percent / TMG / tetrahydrofuran

2.1: H₂; chiral Rh(I) complex / tetrahydrofuran / 20 °C / 760.05 Torr

3.1: DMAP / tetrahydrofuran / 20 °C

3.2: 88 percent / N₂H₄ / methanol / 20 °C

4.1: TFA; DMS / CH₂Cl₂ / 0 °C

5.1: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 0 - 20 °C

With dmap; 1-hydroxy-7-aza-benzotriazole; 2,3-dimercapto-succinic acid; hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja011943e

Reference yield:

2-(3-benzyloxy-4-methoxyphenyl)ethylene (68360-39-4) → (R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester (391213-74-4)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂OsO₂(OH)4; (DHQD)2PHAL / propan-1-ol; H₂O

2: TEMPO; NaOCl; KBr / acetone; H₂O

3: 100 percent / H₂ / Pd/C / ethanol / 760.05 Torr

4: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 0 - 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; 1-hydroxy-7-aza-benzotriazole; potassium dioxotetrahydroxoosmate(VI); hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium bromide; palladium on activated charcoal; In tetrahydrofuran; propan-1-ol; ethanol; water; acetone; 1: Sharpless asymmetric amino-hydroxylation;

DOI:10.1021/ja011943e

Reference yield:

N-chloro-N-sodio-tert-butylcarbamate (73210-14-7) → (R)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-hydroxy-4-methoxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester (391213-74-4)

Guidance literature:

Multi-step reaction with 4 steps

1: K₂OsO₂(OH)4; (DHQD)2PHAL / propan-1-ol; H₂O

2: TEMPO; NaOCl; KBr / acetone; H₂O

3: 100 percent / H₂ / Pd/C / ethanol / 760.05 Torr

4: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 0 - 20 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; 1-hydroxy-7-aza-benzotriazole; potassium dioxotetrahydroxoosmate(VI); hydrogen; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium bromide; palladium on activated charcoal; In tetrahydrofuran; propan-1-ol; ethanol; water; acetone; 1: Sharpless asymmetric amino-hydroxylation;

DOI:10.1021/ja011943e

upstream raw materials:

D-(4-fluoro-3-nitrophenyl)glycine methyl ester

(R)-N-Boc-m-hydroxy-p-methoxyphenyl-Gly

2-(3-benzyloxy-4-methoxyphenyl)ethylene

4-fluoro-3-nitrobenzaldehyde

Downstream raw materials:

(R)-3-(4-Fluoro-3-nitro-phenyl)-2-[(R)-2-(3-hydroxy-4-methoxy-phenyl)-2-(2,2,2-trifluoro-acetylamino)-acetylamino]-propionic acid methyl ester

(8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid

(8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid methylamide

(R)-2-[(R)-2-{3-[3-((S)-tert-Butoxycarbonylamino-methylcarbamoyl-methyl)-5-methoxy-phenoxy]-4-methoxy-phenyl}-2-(2,2,2-trifluoro-acetylamino)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid

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