Sodium Chloride → HCID 67169158, compound

HRID 1475797Notes

Reaction equation

HRID 1475797 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:15][C:16](=[O:26])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([OH:25])[CH:18]=2)[CH2:10][CH2:9][CH:8]([C:11]([F:14])([F:13])[F:12])[CH2:7][CH2:6]1)=[O:4].[O:27]1[CH2:30][CH:29]([C:31]2[CH:32]=[C:33]([CH2:37][CH2:38]OS(C3C=CC(C)=CC=3)(=O)=O)[CH:34]=[CH:35][CH:36]=2)[CH2:28]1.C([O-])([O-])=O.[K+].[K+].[Na+].[Cl-]>CC(=O)OCC.CN(C=O)C>[CH3:1][O:2][C:3]([C:5]1([NH:15][C:16](=[O:26])[C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:38][CH2:37][C:33]3[CH:34]=[CH:35][CH:36]=[C:31]([CH:29]4[CH2:28][O:27][CH2:30]4)[CH:32]=3)[CH:18]=2)[CH2:6][CH2:7][CH:8]([C:11]([F:14])([F:13])[F:12])[CH2:9][CH2:10]1)=[O:4]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 11430Potassium CarbonateHCID 671711291-(3-Hydroxy-4-methoxy-benzoylamino)-4-trifluoromethyl-cyclohexanecarboxylic Acid Methyl EsterHCID 86672565HCID 86672565, compound2×

Product 1

HCID 67169158HCID 67169158, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

60 mg of 1-(3-Hydroxy-4-methoxy-benzoylamino)-4-trifluoromethyl-cyclohexanecarboxylic acid methyl ester, 53 mg of toluene-4-sulfonic acid 2-(3-oxetan-3-yl-phenyl)-ethyl ester, and 66 mg of K2CO3 were added to 3 ml of DMF and the mixture was stirred for 8 h at 40° C. Then, 27 mg of toluene-4-sulfonic acid 2-(3-oxetan-3-yl-phenyl)-ethyl ester were added and stirring was continued for 8 h at 40° C. Then, 10 ml of EA and 15 ml of a half-saturated aqueous NaCl-solution were added. The layers were separated and the aqueous layer was extracted twice using 10 ml of EA each. The combined organic layer was then dried using MgSO4 and evaporated. Chromatography on silica gel using EA/HEP 1:1 yielded 77 mg of the title compound, amorphous solid.

Workup

  1. stirringstirring
  2. waitwas continued for 8 h at 40° C
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted twice
  5. customThe combined organic layer was then dried
  6. customevaporated

Sources & evidence

ORD record
ord-950d261008754dca9a4d36c7813eebcb
Source dataset
uspto-grants-2015_04
Patent number
US09018383B2

Reaction notes

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