Ethyl 5-(phenylmethoxy)-1H-indole-2-carboxylate → HCID 68466524, compound

HRID 2105350Notes

Reaction equation

HRID 2105350 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[C@H:34]([CH3:35])[CH2:33]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]([CH2:35][C@H:34]([NH:30][C:28]([O:27][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:29])[CH3:33])[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 46172873(4R)-2,2-Dioxido-4-methyl-1,2,3-oxathiazolidine,N-BOC protected

Product 1

HCID 68466524HCID 68466524, compoundYield 100%

Procedure

The title compound was synthesized in analogy to example 1, intermediate b), from ethyl 5-benzyloxyindole-2-carboxylate (commercially available), (R)-4-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 light yellow solid (>100%). The so-obtained product was used in the next step without further purification.

Sources & evidence

ORD record
ord-568f7ef53dd54e5f87cb98bb434c5c35
Source dataset
uspto-grants-2009_08
Patent number
US07579351B2

Reaction notes

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