(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxide → (R)-1-(2-tert-Butoxycarbonylamino-1-methyl-ethyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester

HRID 11927Notes

Reaction equation

HRID 11927 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:14][C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:2].CC(C)([O-])C.[K+].[C:21]([O:25][C:26]([N:28]1[CH2:32][C@H:31]([CH3:33])OS1(=O)=O)=[O:27])([CH3:24])([CH3:23])[CH3:22]>>[CH2:1]([O:3][C:4]([C:6]1[N:14]([C@H:31]([CH3:33])[CH2:32][NH:28][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:27])[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 11195739(s)-Tert-butyl 5-methyl-1,2,3-oxathiazolidine-3-carboxylate 2,2-dioxideHCID 21868741Ethyl 1H-pyrrolo(2,3-b)pyridine-2-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 69556545(R)-1-(2-tert-Butoxycarbonylamino-1-methyl-ethyl)-1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester

Procedure

This compound was prepared in analogy to Example 1 intermediate a), from 1H-pyrrolo[2,3-b]pyridine-2-carboxylic acid ethyl ester, potassium tert-butoxide and (S)-5-methyl-2,2-dioxo-[1,2,3]oxathiazolidine-3-carboxylic acid tert-butyl ester.

Sources & evidence

ORD record
ord-3096397b79924ba2b3dce04ecbaf743c
Source dataset
uspto-grants-2006_08
Patent number
US07098337B2

Reaction notes

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