(3S)-4-(1-formyl-1H-indol-3-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)butanoic acid

Base Information

Chemical Name:(3S)-4-(1-formyl-1H-indol-3-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)butanoic acid
CAS No.:914939-87-0
Molecular Formula:C₂₂H₂₂N₂O₅
Molecular Weight:394.427
Hs Code.:

Synonyms:(3S)-4-(1-formyl-1H-indol-3-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)butanoic acid

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Chemical Property of (3S)-4-(1-formyl-1H-indol-3-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)butanoic acid

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Technology Process of (3S)-4-(1-formyl-1H-indol-3-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)butanoic acid

There total 4 articles about (3S)-4-(1-formyl-1H-indol-3-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)butanoic acid 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: 68.0%

: 914939-86-9
phenylmethyl {(1S)-3-diazo-1-[(1-formyl-1H-indol-3-yl)methyl]-2-oxopropyl}methylcarbamate

: 914939-87-0
(3S)-4-(1-formyl-1H-indol-3-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)butanoic acid

Guidance literature:: With silver trifluoroacetate; In 1,4-dioxane; water; for 0.5h; sonication;
DOI:10.1002/hlca.200690235

Reference yield:

: 70601-16-0
1-formyl-N-[(phenylmethoxy)carbonyl]-L-tryptophan

: 914939-87-0
(3S)-4-(1-formyl-1H-indol-3-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)butanoic acid

Guidance literature:: Multi-step reaction with 4 steps

1.1: CSA / toluene / Heating

2.1: Et₃SiH; CF₃COOH / CH₂Cl₂

3.1: ClCOOEt; N-methylmorpholine / tetrahydrofuran / 0.25 h / -15 °C

3.2: 56 percent / tetrahydrofuran; CH₂Cl₂ / -15 - 20 °C

4.1: 68 percent / CF₃COOAg / dioxane; H₂O / 0.5 h / sonication

With 4-methyl-morpholine; triethylsilane; silver trifluoroacetate; chloroformic acid ethyl ester; trifluoroacetic acid; camphor-10-sulfonic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; toluene; 4.1: Wolff rearrangement;
DOI:10.1002/hlca.200690235

Reference yield:

: 475296-63-0
(2S)-3-(1-formyl-1H-indol-3-yl)-2-(methyl{[(phenylmethyl)oxy]carbonyl}amino)propanoic acid

: 914939-87-0
(3S)-4-(1-formyl-1H-indol-3-yl)-3-(methyl{[(phenylmethyl)oxy]carbonyl}amino)butanoic acid

Guidance literature:: Multi-step reaction with 2 steps

1.1: ClCOOEt; N-methylmorpholine / tetrahydrofuran / 0.25 h / -15 °C

1.2: 56 percent / tetrahydrofuran; CH₂Cl₂ / -15 - 20 °C

2.1: 68 percent / CF₃COOAg / dioxane; H₂O / 0.5 h / sonication

With 4-methyl-morpholine; silver trifluoroacetate; chloroformic acid ethyl ester; In tetrahydrofuran; 1,4-dioxane; water; 2.1: Wolff rearrangement;
DOI:10.1002/hlca.200690235