Potassium Carbonate → HCID 11657071, compound

HRID 229881Notes

Reaction equation

HRID 229881 reaction equation
[F:1][C:2]([F:43])([F:42])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[C:13]1[N:17]([CH2:18][C@H:19]2[CH2:23][CH2:22][CH2:21][O:20]2)[C:16]([CH3:24])=[C:15]([C:25]([NH:27][CH:28]2[CH:33]3[C:34]([CH3:36])([CH3:35])[C:30]([CH3:37])([CH2:31][CH2:32]3)[CH:29]2[O:38]C(=O)C)=[O:26])[CH:14]=1.C([O-])([O-])=O.[K+].[K+]>CO>[OH:38][CH:29]1[C:30]2([CH3:37])[C:34]([CH3:36])([CH3:35])[CH:33]([CH2:32][CH2:31]2)[CH:28]1[NH:27][C:25]([C:15]1[CH:14]=[C:13]([C:4]2[CH:5]=[C:6]([C:9]([F:10])([F:11])[F:12])[CH:7]=[CH:8][C:3]=2[C:2]([F:43])([F:1])[F:42])[N:17]([CH2:18][C@H:19]2[CH2:23][CH2:22][CH2:21][O:20]2)[C:16]=1[CH3:24])=[O:26]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 11592524HCID 11592524, compound

Product 1

HCID 11657071HCID 11657071, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of acetic acid 3-({5-(2,5-bis-trifluoromethyl-phenyl)-2-methyl-1-[(R)-1-(tetrahydro-furan-2-yl)methyl]-1H-pyrrole-3-carbonyl}-amino)-1,7,7-trimethyl-bicyclo[2.2.1]hept-2-yl ester (60 mg) in MeOH (2 mL) was added 15 μL of a 1N K2CO3 solution. After 18 hours the reaction mixture was extracted with ethyl acetate and the organic phases were washed with brine, dried over sodium sulfate and filtered. Removal of the volatiles in vacuo and chromatography of the crude residue afforded the title compound (54 mg), MS (ISP) 631.5 (M+H)+.

Workup

  1. extractionAfter 18 hours the reaction mixture was extracted with ethyl acetate
  2. washthe organic phases were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customRemoval of the volatiles in vacuo and chromatography of the crude residue

Sources & evidence

ORD record
ord-7618248d0984484a9283dc5e127585bc
Source dataset
uspto-grants-2009_07
Patent number
US07563910B2

Reaction notes

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