Ethyl Acetate → HCID 178520335, compound

HRID 916053Notes

Reaction equation

HRID 916053 reaction equation
C[O:2][C:3]([C:5]1[N:6]=[N:7][N:8]([C@H:10]2[CH2:15][CH2:14][C@@H:13]([NH:16][C:17](=[O:27])[CH2:18][C:19]3[C:24]([F:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])[CH2:12][CH2:11]2)[CH:9]=1)=[O:4].O[Li].O.CCOC(C)=O>C1COCC1.CO.O>[Cl:26][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]([F:25])[C:19]=1[CH2:18][C:17]([NH:16][C@@H:13]1[CH2:14][CH2:15][C@H:10]([N:8]2[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[N:6]=[N:7]2)[CH2:11][CH2:12]1)=[O:27]

Participants

7

Reactant 3

HCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 178498824HCID 178498824, compound

Product 1

HCID 178520335HCID 178520335, compoundYield 88.4%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

1-{cis-4-[2-(2-Chloro-6-fluoro-phenyl)-acetylamino]-cyclohexyl}-1H-[1,2,3]triazole-4-carboxylic acid methyl ester (400 mg) was dissolved in a mixture of THF (3.2 ml)/MeOH (3.2 ml)/H2O (1.6 ml) and LiOH.H2O (43 mg) was added. The reaction mixture was stirred 1 h at 60° C., then it was poured on a mixture of H2O (35 ml) and EtOAc (35 ml). The aqueous layer was collected, acidified with 1 M HCl to pH<4 and extracted with EtOAc (2×35 ml). After drying over Na2SO4 the solvent was evaporated to yield 341 mg (88%) of product. White powder. MS 379.1 (100, [M−H]−).

Workup

  1. additionwas added
  2. customThe aqueous layer was collected
  3. extractionextracted with EtOAc (2×35 ml)
  4. dry with materialAfter drying over Na2SO4 the solvent
  5. customwas evaporated

Sources & evidence

ORD record
ord-ebc7883029db41de950f0f07e10a88d0
Source dataset
uspto-grants-2007_09
Patent number
US07268154B2

Reaction notes

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