(S)-N^α-tert-butoxycarbonyl-m-{[(trifluoromethyl)sulfonyl]oxy}phenylalanine methyl ester

Base Information

• Chemical Name: (S)-N^α-tert-butoxycarbonyl-m-{[(trifluoromethyl)sulfonyl]oxy}phenylalanine methyl ester
• CAS No.: 447461-07-6
• Molecular Formula: C₁₆H₂₀F₃NO₇S
• Molecular Weight: 427.399

Synonyms:(S)-N^α-tert-butoxycarbonyl-m-{[(trifluoromethyl)sulfonyl]oxy}phenylalanine methyl ester

Chemical Property of (S)-N^α-tert-butoxycarbonyl-m-{[(trifluoromethyl)sulfonyl]oxy}phenylalanine methyl ester

Chemical Property:

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Technology Process of (S)-N^α-tert-butoxycarbonyl-m-{[(trifluoromethyl)sulfonyl]oxy}phenylalanine methyl ester

There total 5 articles about (S)-N^α-tert-butoxycarbonyl-m-{[(trifluoromethyl)sulfonyl]oxy}phenylalanine 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: 93.0%

trifluoromethylsulfonic anhydride (358-23-6) + 2S-tert-butoxycarbonylamino-3-(3-hydroxyphenyl)propionic acid methyl ester (900800-02-4) → (S)-Nα-tert-butoxycarbonyl-m-{[(trifluoromethyl)sulfonyl]oxy}phenylalanine methyl ester (447461-07-6)

Guidance literature:

In pyridine; dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(02)00162-X

Reference yield:

3-Benzyloxybenzaldehyde (1700-37-4) → (S)-Nα-tert-butoxycarbonyl-m-{[(trifluoromethyl)sulfonyl]oxy}phenylalanine methyl ester (447461-07-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / DBU / CH₂Cl₂ / 4 h / 20 °C

2: 100 percent / H₂ / [(S,S)-Et-Du-PHOS)-Rh]OTf / methanol / 24 h / 3361.46 Torr

3: 99 percent / H₂ / 10 percent Pd/C / methanol / 9 h / 3102.89 Torr

4: 93 percent / pyridine; CH₂Cl₂ / 0.5 h / 0 °C

With hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In pyridine; methanol; dichloromethane;

DOI:10.1016/S0040-4020(02)00162-X

Reference yield:

trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate (121056-95-9,89524-98-1) → (S)-Nα-tert-butoxycarbonyl-m-{[(trifluoromethyl)sulfonyl]oxy}phenylalanine methyl ester (447461-07-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / DBU / CH₂Cl₂ / 4 h / 20 °C

2: 100 percent / H₂ / [(S,S)-Et-Du-PHOS)-Rh]OTf / methanol / 24 h / 3361.46 Torr

3: 99 percent / H₂ / 10 percent Pd/C / methanol / 9 h / 3102.89 Torr

4: 93 percent / pyridine; CH₂Cl₂ / 0.5 h / 0 °C

With hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In pyridine; methanol; dichloromethane;

DOI:10.1016/S0040-4020(02)00162-X

upstream raw materials:

trifluoromethylsulfonic anhydride

2S-tert-butoxycarbonylamino-3-(3-hydroxyphenyl)propionic acid methyl ester

3-Benzyloxybenzaldehyde

trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate

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