2-(1-Carboxy-2-ethyl-cyclopropylcarbamoyl)-4-(6-methoxy-isoquinolin-1-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester → 2-[2-Ethyl-1-(1-methoxycarbonyl-cyclopropoxysulfonylaminocarbonyl)-cyclopropylcarbamoyl]-4-(6-methoxy-isoquinolin-1-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)[CH:17]=[CH:16][N:15]=2)[CH2:10][CH:9]1[C:26](=[O:36])[NH:27][C:28]1([C:33](O)=[O:34])[CH2:30][CH:29]1[CH2:31][CH3:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:37][O:38][C:39]([C:41]1([O:44][S:45](=[O:48])(=[O:47])[NH2:46])[CH2:43][CH2:42]1)=[O:40].S(=O)(=O)(O)N>>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([O:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)[CH:17]=[CH:16][N:15]=2)[CH2:10][CH:9]1[C:26](=[O:36])[NH:27][C:28]1([C:33]([NH:46][S:45]([O:44][C:41]2([C:39]([O:38][CH3:37])=[O:40])[CH2:42][CH2:43]2)(=[O:48])=[O:47])=[O:34])[CH2:30][CH:29]1[CH2:31][CH3:32])=[O:7])([CH3:2])([CH3:3])[CH3:4]Participants
3
Reactant 2
Product 1
Procedure
2-[2-Ethyl-1-(1-methoxycarbonyl-cyclopropoxysulfonylaminocarbonyl)-cyclopropylcarbamoyl]-4-(6-methoxy-isoquinolin-1-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester was prepared according to the method presented in Example 27. Treatment of 2-(1-carboxy-2-ethyl-cyclopropylcarbamoyl)-4-(6-methoxy-isoquinolin-1-yloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (0.10 mmol) occurred under the same conditions, adjusted for scale with the exception of utilizing sulfamic acid 1-sulfamoyloxy-cyclopropanecarboxylic acid methyl ester (40 mg, 60%): LCMS found 676.2 [M+H]+.
Sources & evidence
- ORD record
- ord-20a823ae22ad46988ecd867836fda0c6
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513186B2
Reaction notes
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