1(R)-4'(S)-benzyloxycarbonylamino-4'-(1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)butyric acid tert-butyl ester

Base Information

Chemical Name:1(R)-4'(S)-benzyloxycarbonylamino-4'-(1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)butyric acid tert-butyl ester
CAS No.:153037-22-0
Molecular Formula:C₂₇H₃₃N₃O₄
Molecular Weight:463.577
Hs Code.:

Synonyms:1(R)-4'(S)-benzyloxycarbonylamino-4'-(1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)butyric acid tert-butyl ester

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Chemical Property of 1(R)-4'(S)-benzyloxycarbonylamino-4'-(1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)butyric acid tert-butyl ester

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Technology Process of 1(R)-4'(S)-benzyloxycarbonylamino-4'-(1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)butyric acid tert-butyl ester

There total 4 articles about 1(R)-4'(S)-benzyloxycarbonylamino-4'-(1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)butyric acid tert-butyl 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: 81.0%

: 61-54-1
tryptamine

: 92506-78-0
4(S)-benzyloxycarbonylamino-5-oxo-pentanoic acid tert-butyl ester

: 153037-22-0
1(R)-4'(S)-benzyloxycarbonylamino-4'-(1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)butyric acid tert-butyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at -40 ℃; for 2h;
DOI:10.1016/S0040-4020(00)00165-4

Reference yield: 30.0%

: 61-54-1
tryptamine

: 92506-78-0
4(S)-benzyloxycarbonylamino-5-oxo-pentanoic acid tert-butyl ester

: 153037-22-0
1(R)-4'(S)-benzyloxycarbonylamino-4'-(1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)butyric acid tert-butyl ester

: 3a(R)-4(S)-1,2,3,3a,4,5-hexahydro-4-(tert-butoxycarbonylpropyl)-5-(benzyloxycarbonyl)-pyrrolo[2',3':3,4]pyrrolo[2,3-b]indole

: C₂₇H₃₃N₃O₄

: 1(S)-4'(S)-benzyloxycarbonylamino-4'-(1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)butyric acid tert-butyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 40 ℃; for 0.25h; Further byproducts given;
DOI:10.1016/S0040-4020(00)00165-4

Reference yield:

: 3886-08-6
5-tert-butyl N-benzyloxycarbonyl-L-glutamate

: 153037-22-0
1(R)-4'(S)-benzyloxycarbonylamino-4'-(1,2,3,4-tetrahydro-1H-β-carbolin-1-yl)butyric acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: N-methylmorpholine; iso-butyl chloroformate / CH₂Cl₂ / 0.5 h / -15 °C

1.2: 96 percent / CH₂Cl₂ / 2 h / -15 - 20 °C

2.1: 99 percent / LiAlH₄ / diethyl ether / 2.67 h / -40 °C

3.1: 81 percent / TFA / CH₂Cl₂ / 2 h / -40 °C

With 4-methyl-morpholine; lithium aluminium tetrahydride; trifluoroacetic acid; isobutyl chloroformate; In diethyl ether; dichloromethane; 1.1: Substitution / 1.2: Substitution / 2.1: Reduction / 3.1: Pictet-Spengler reaction;
DOI:10.1016/S0040-4020(00)00165-4