Potassium Carbonate → 1-[3-(2,2-Difluoro-2-phenyl-ethoxy)-4-methoxy-benzoylamino]-cycloheptanecarboxylic acid methyl ester

HRID 1475715Notes

Reaction equation

HRID 1475715 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:12][C:13](=[O:23])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([OH:22])[CH:15]=2)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[F:30][C:31]([F:47])([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[CH2:32]OS(C(F)(F)F)(=O)=O>CC(C)=O.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1([NH:12][C:13](=[O:23])[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH2:32][C:31]([F:47])([F:30])[C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[CH:15]=2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11]1)=[O:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 22138897HCID 22138897, compoundHCID 67170485HCID 67170485, compound

Product 1

HCID 671709261-[3-(2,2-Difluoro-2-phenyl-ethoxy)-4-methoxy-benzoylamino]-cycloheptanecarboxylic acid methyl esterYield 75.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-(3-hydroxy-4-methoxy-benzoylamino)-cycloheptanecarboxylic acid methyl ester (80 mg, 0.249 mmol) and potassium carbonate (83 mg, 0.60 mmol) in 0.5 ml of acetone and 0.5 ml of DMF was added slowly a solution of the compound of step 1 (0.22 g, 0.374 mmol) as solution in acetone. The mixture was stirred for 3 d at room temperature and then evaporated. The residue was purified by preparative RP HPLC (water/ACN gradient) to give the title compound (87 mg).

Workup

  1. customevaporated
  2. customThe residue was purified by preparative RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-60cdd71eb4a84fb0bc444c04d2dfa176
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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