Sulfamic acid 2,2,2-trifluoro-1,1-dimethyl-ethyl ester → 2-[2-Ethyl-1-(2,2,2-trifluoro-1,1-dimethyl-ethoxysulfonylaminocarbonyl)-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]([OH:35])=O)[CH2:30][CH:29]1[CH2:31][CH3:32])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:37][C:38]([F:48])([F:47])[C:39]([O:42][S:43](=[O:46])(=[O:45])[NH2:44])([CH3:41])[CH3:40]>>[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:44][S:43]([O:42][C:39]([CH3:41])([CH3:40])[C:38]([F:37])([F:48])[F:47])(=[O:45])=[O:46])=[O:35])[CH2:30][CH:29]1[CH2:31][CH3:32])=[O:7])([CH3:3])([CH3:4])[CH3:2]Participants
3
Reactant 2
Product 1
Procedure
2-[2-Ethyl-1-(2,2,2-trifluoro-1,1-dimethyl-ethoxysulfonylaminocarbonyl)-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 (2.01 mmol) occurred under the same conditions, adjusted for scale with the exception of utilizing sulfamic acid 2,2,2-trifluoro-1,1-dimethyl-ethyl ester to afford acylsulfamate (450 mg, 65%): LCMS found 688.9 [M+H]+.
Sources & evidence
- ORD record
- ord-fbb4cc17ad1a481d81b0f6151bed3dcc
- Source dataset
- uspto-grants-2013_08
- Patent number
- US08513186B2
Reaction notes
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