Diisopropylethylamine → HCID 131723093, compound

HRID 1250390Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]#[N:26])[CH:20]=1)[C:13]([C:27]([OH:29])=[O:28])=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:30]1([C@H:36]([NH2:38])[CH3:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.C1(P([N:53]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.C(N(C(C)C)CC)(C)C>>[C:27]([OH:29])(=[O:28])[CH3:13].[C:30]1([C@H:36]([NH:38][C:27]([C:13]2[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25](=[NH:26])[NH2:53])[CH:20]=3)[C:15]3[C:11]([CH:12]=2)=[CH:10][C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[CH:17][CH:16]=3)=[O:29])[CH3:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

Reactant 4

HCID 81531Diisopropylethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 6431891-Phenethylamine, (+)-

HCID 10959912HCID 10959912, compound

Product 1

HCID 131723093HCID 131723093, compoundYield 73%

Procedure

This compound was prepared from 5-benzyloxy-1-(3-cyano-benzyl)-1H-indole-2-carboxylic acid and (R)-1-phenyl-ethyl-amine by using diphenylphosphoryl azide and diisopropylethylamine as described in example 3/1. The crude material was purified by flash chromatography on silica gel with dichloromethane to give the desired product in 73% yield. M.p. 169-170° C. MS: 486.3 (M+H+).

Workup

customThe crude material was purified by flash chromatography on silica gel with dichloromethane

Sources & evidence

ORD record: ord-a08e1803e8df4531aba39e7321af44ab
Source dataset: uspto-grants-2002_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06337344B1

Reaction notes

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