Water → 2-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-[2-(3-fluoro-phenyl)-7-methoxy-8-methyl-quinazolin-4-yloxy]-cyclopentanecarboxylic acid

HRID 1443503Notes

Reaction equation

HRID 1443503 reaction equation
C([O:5][C:6]([CH:8]1[CH2:12][CH:11]([O:13][C:14]2[C:23]3[C:18](=[C:19]([CH3:26])[C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)[N:17]=[C:16]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=3)[N:15]=2)[CH2:10][CH:9]1[C:34](=[O:46])[NH:35][C:36]1([C:41]([O:43][CH2:44][CH3:45])=[O:42])[CH2:38][CH:37]1[CH:39]=[CH2:40])=[O:7])(C)(C)C.O>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH2:44]([O:43][C:41]([C:36]1([NH:35][C:34]([CH:9]2[CH2:10][CH:11]([O:13][C:14]3[C:23]4[C:18](=[C:19]([CH3:26])[C:20]([O:24][CH3:25])=[CH:21][CH:22]=4)[N:17]=[C:16]([C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([F:33])[CH:28]=4)[N:15]=3)[CH2:12][CH:8]2[C:6]([OH:7])=[O:5])=[O:46])[CH2:38][CH:37]1[CH:39]=[CH2:40])=[O:42])[CH3:45]

Participants

5

Reactant 2

HCID 962WaterHCID 684124612-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-[2-(3-fluoro-phenyl)-7-methoxy-8-methyl-quinazolin-4-yloxy]-cyclopentanecarboxylic acid tert-butyl ester

Product 1

HCID 686865802-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-[2-(3-fluoro-phenyl)-7-methoxy-8-methyl-quinazolin-4-yloxy]-cyclopentanecarboxylic acidYield 99.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 155 (0.896 g, 1.41 mmol) was dissolved in a mixture of DCM (30 mL), TFA (10 mL), a few drops of TES and a drop of H2O. The reaction was stirred for 30 minutes followed by removal of solvent by evaporation. The crude residue was partitioned between CHCl3 and saturated NaHCO3 (aq). The organic phase was dried (Na2SO4) and evaporated which gave the compound (0.81 g, 99%) as a white solid.

Workup

  1. customfollowed by removal of solvent by evaporation
  2. customThe crude residue was partitioned between CHCl3 and saturated NaHCO3 (aq)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated which

Sources & evidence

ORD record
ord-320d2010d5314c698cce43f0085a742f
Source dataset
uspto-grants-2010_02
Patent number
US07659245B2

Reaction notes

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