5-Chloro-2-thiophenecarboxylic acid → 3-{2-[(5-Chloro-thiophene-2-carbonyl)-amino]-ethanesulfonylamino}-azetidine-1-carboxylic acid tert-butyl ester

HRID 416500Notes

Reaction equation

HRID 416500 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:20][CH:19]([NH:21][S:22]([CH2:25][CH2:26][NH2:27])(=[O:24])=[O:23])[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]>>[C:10]([O:14][C:15]([N:17]1[CH2:20][CH:19]([NH:21][S:22]([CH2:25][CH2:26][NH:27][C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:9])(=[O:24])=[O:23])[CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 950485-Chloro-2-thiophenecarboxylic acidHCID 666246733-(2-Amino-ethanesulfonylamino)-azetidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 666248523-{2-[(5-Chloro-thiophene-2-carbonyl)-amino]-ethanesulfonylamino}-azetidine-1-carboxylic acid tert-butyl ester

Procedure

3-{2-[(5-Chloro-thiophene-2-carbonyl)-amino]-ethanesulfonylamino}-azetidine-1-carboxylic acid tert-butyl ester was prepared by an analogous procedure as described in example 5 iii) starting from 240 mg (1.3 equiv.) 5-chloro-thiophene-2-carboxylic acid and 308 mg (1.1 mmol) 3-(2-amino-ethanesulfonylamino)-azetidine-1-carboxylic acid tert-butyl ester. Final purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA) gave pure 3-{2-[(5-chloro-thiophene-2-carbonyl)-amino]-ethanesulfonylamino}-azetidine-1-carboxylic acid tert-butyl ester. The title compound was obtained in form of a colorless amorphous material.

Workup

  1. custom3-{2-[(5-Chloro-thiophene-2-carbonyl)-amino]-ethanesulfonylamino}-azetidine-1-carboxylic acid tert-butyl ester was prepared by an analogous procedure
  2. customFinal purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA)

Sources & evidence

ORD record
ord-044f60e7cabe47c899d86e8626fc3e56
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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