Trifluoromethanesulfonic acid → 2-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(7-methoxy-2-phenyl-quinazolin-4-yloxy)-cyclopentanecarboxylic acid

HRID 1443431Notes

Reaction equation

HRID 1443431 reaction equation
C([O:5][C:6]([CH: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)[N:17]=[C:16]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:15]=2)[CH2:10][CH:9]1[C:32](=[O:44])[NH:33][C:34]1([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH2:36][CH:35]1[CH:37]=[CH2:38])=[O:7])(C)(C)C.FC(F)(F)S(O)(=O)=O>ClCCl.C([SiH](CC)CC)C>[CH2:42]([O:41][C:39]([C:34]1([NH:33][C:32]([CH:9]2[CH2:10][CH:11]([O:13][C:14]3[C:23]4[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=4)[N:17]=[C:16]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:15]=3)[CH2:12][CH:8]2[C:6]([OH:7])=[O:5])=[O:44])[CH2:36][CH:35]1[CH:37]=[CH2:38])=[O:40])[CH3:43]

Participants

5

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 684230722-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(7-methoxy-2-phenyl-quinazolin-4-yloxy)-cyclopentanecarboxylic acid tert-butyl ester

Product 1

HCID 684209862-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(7-methoxy-2-phenyl-quinazolin-4-yloxy)-cyclopentanecarboxylic acidYield 99.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 12052TriethylsilaneSolvent

Procedure

Compound 16 (780 mg, 1.29 mmol) was dissolved in dichloromethane (20 mL) and triethylsilane (0.4 mL). Trifluoromethanesulfonic acid was added dropwise at room temperature. The mixture was then left for 2 h at room temperature. Removal of the solvent gave pure title product (700 mg, 99%) MS (M+H)+ 546.

Workup

  1. customRemoval of the solvent

Sources & evidence

ORD record
ord-0c676a151ff946aca1977942ae6014cf
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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