Ethyl 5-(phenylmethoxy)-1H-indole-2-carboxylate → 5-Benzyloxy-1-((S)-2-tert-butoxycarbonylamino-1-methyl-ethyl)-1H-indole-2-carboxylic acid ethyl ester

HRID 2105344Notes

Reaction equation

HRID 2105344 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:23]([O:27][C:28]([N:30]1[CH2:34][C@@H:33]([CH3:35])OS1(=O)=O)=[O:29])([CH3:26])([CH3:25])[CH3:24].CC(C)([O-])C.[K+]>>[CH2:21]([O:20][C:18]([C:13]1[N:14]([C@@H:33]([CH3:35])[CH2:34][NH:30][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:29])[C:15]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[CH:17][CH:16]=2)=[O:19])[CH3:22]

Participants

4

Reactant 3

HCID 95721Ethyl 5-(phenylmethoxy)-1H-indole-2-carboxylateHCID 23665647Potassium tert-butoxideHCID 866129301,2,3-Oxathiazolidine-3-carboxylic acid, 5-methyl-, 1,1-dimethylethyl ester, 2,2-dioxide, (5R)-

Product 1

HCID 684623725-Benzyloxy-1-((S)-2-tert-butoxycarbonylamino-1-methyl-ethyl)-1H-indole-2-carboxylic acid ethyl esterYield 100%

Procedure

The title compound was synthesized in analogy to example 8, intermediate a), from ethyl 5-benzyloxyindole-2-carboxylate (commercially available), (R)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester (prepared according to WO02/010169) and potassium tert-butoxide, to give the desired compound as a yellow solid (100%).

Sources & evidence

ORD record
ord-e487b54e3c724287ad57e2e09cca36d6
Source dataset
uspto-grants-2009_08
Patent number
US07579351B2

Reaction notes

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