2-[3-(S)-Amino-2-oxo-pyrrolidin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester → HCID 54483439, compound

HRID 651676Notes

Reaction equation

HRID 651676 reaction equation
[Cl:1][C:2]1[S:6][C:5]([CH:7]=[CH:8][S:9](Cl)(=[O:11])=[O:10])=[CH:4][CH:3]=1.[C:13]([O:17][C:18]([N:20]1[C:28]2[CH:27]=[CH:26][N:25]=[CH:24][C:23]=2[CH:22]=[C:21]1[CH2:29][N:30]1[CH2:34][CH2:33][C@H:32]([NH2:35])[C:31]1=[O:36])=[O:19])([CH3:16])([CH3:15])[CH3:14]>>[C:13]([O:17][C:18]([N:20]1[C:28]2[CH:27]=[CH:26][N:25]=[CH:24][C:23]=2[CH:22]=[C:21]1[CH2:29][N:30]1[CH2:34][CH2:33][C@H:32]([NH:35][S:9]([CH:8]=[CH:7][C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)(=[O:11])=[O:10])[C:31]1=[O:36])=[O:19])([CH3:16])([CH3:14])[CH3:15]

Participants

3

Reactant 2

HCID 543682692-[3-(S)-Amino-2-oxo-pyrrolidin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl esterHCID 544630642-(5-Chlorothiophen-2-yl)ethenesulfonyl chloride

Product 1

HCID 54483439HCID 54483439, compound

Procedure

The title compound is prepared as described in EXAMPLE 56, Part A using 2-(5-chlorothiophen-2-yl)-ethenesulfonyl chloride and 2-[3-(S)-amino-2-oxo-pyrrolidin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester as starting material. The crude product can be purified by column chromatography eluting with 5% MeOH/CH2Cl2 to give the title compound as a white solid or used in the subsequent step after an aqueous work-up without further purification.

Workup

  1. customThe title compound is prepared
  2. customThe crude product can be purified by column chromatography
  3. washeluting with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-85602bc39e8a40c38a814bfd6ca128d8
Source dataset
uspto-grants-2001_08
Patent number
US06281227B1

Reaction notes

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