(R)-[(tert-butoxycarbonyl)-[2-(tertbutyidimethylsilanyloxy)-2-(3-chlorophenyl)ethyl]amino}acetaldehyde → (R)-5-[3-[[2-[[2-(3-Chlorophenyl)-2-[[(tert-butyl)dimethylsilyl]oxy]ethyl][(tert-butoxy)carbonyl]amino]ethyl]amino]phenyl]-2,3-dihydro-7-benzofurancarboxylic acid methyl ester

HRID 1069095Notes

Reaction equation

HRID 1069095 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH2:20])[CH:15]=2)[CH:6]=1)=[O:4].[C:21]([O:25][C:26]([N:28]([CH2:46][CH:47]=O)[CH2:29][C@H:30]([O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>CCCCCC.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[C:13]2[O:12][CH2:11][CH2:10][C:9]=2[CH:8]=[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][CH2:47][CH2:46][N:28]([CH2:29][C@@H:30]([C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[CH:32]=3)[O:38][Si:39]([C:42]([CH3:43])([CH3:44])[CH3:45])([CH3:41])[CH3:40])[C:26]([O:25][C:21]([CH3:22])([CH3:23])[CH3:24])=[O:27])[CH:15]=2)[CH:6]=1)=[O:4]

Participants

4

Reactant 2

HCID 20666899(R)-[(tert-butoxycarbonyl)-[2-(tertbutyidimethylsilanyloxy)-2-(3-chlorophenyl)ethyl]amino}acetaldehydeHCID 697796895-(3-Aminophenyl)-2,3-dihydro-7-benzofurancarboxylic acid methyl ester

Product 1

HCID 69779821(R)-5-[3-[[2-[[2-(3-Chlorophenyl)-2-[[(tert-butyl)dimethylsilyl]oxy]ethyl][(tert-butoxy)carbonyl]amino]ethyl]amino]phenyl]-2,3-dihydro-7-benzofurancarboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

TLC Rf (4:1 hexane/ethyl acetate)=0.14; from 5-(3-aminophenyl)-2,3-dihydro-7-benzofurancarboxylic acid methyl ester (500 mg) and (R)-[(tert-butoxycarbonyl)-[2-(tert-butyldimethylsilanoxy)-2-(3-chlorophenyl)ethyl]amino]-acetaldehyde (1.3 g).

Sources & evidence

ORD record
ord-39e2169e80134b91a47e501a15eaa194
Source dataset
uspto-grants-2001_06
Patent number
US06251925B1

Reaction notes

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