Water → HCID 67289520, compound

HRID 511863Notes

Reaction equation

HRID 511863 reaction equation
Br[CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].C(=O)([O-])[O-].[K+].[K+].[OH:16][C:17]1[CH:22]=[CH:21][C:20]([C@H:23]2[CH2:25][C@@H:24]2[C:26]([NH:28][C@@H:29]([C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][C:39]([F:42])([F:41])[F:40])=[CH:33][N:32]=2)[CH3:30])=[O:27])=[CH:19][CH:18]=1.O>ClCCl>[F:42][C:39]([F:40])([F:41])[CH2:38][O:37][C:34]1[CH:35]=[CH:36][C:31]([C@H:29]([NH:28][C:26]([C@H:24]2[CH2:25][C@@H:23]2[C:20]2[CH:19]=[CH:18][C:17]([O:16][CH2:2][C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4])=[CH:22][CH:21]=2)=[O:27])[CH3:30])=[N:32][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 68452306HCID 68452306, compound

Product 1

HCID 67289520HCID 67289520, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl 2-bromoacetate (0.063 ml, 0.434 mmol), potassium carbonate (109 mg, 0.789 mmol) and (1S*,2S*)-2-(4-hydroxyphenyl)-N-((R)-1-(5-(2,2,2-trifluoroethoxy)pyridin-2-yl)ethyl)cyclopropanecarboxamide (150 mg, 0.394 mmol) in dichloromethane (4 ml) was refluxed with stirring for 3 hours. After cooling to room temperature, the mixture was poured into water, and the aqueous layer was extracted with ethyl acetate, dried over magnesium sulfate and concentrated in vacuo. The residue was recrystallized from tetrahydrofuran/hexane. To give 137 mg (70% yield) of title compound as a white crystal:

Workup

  1. temperaturewas refluxed
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was recrystallized from tetrahydrofuran/hexane

Sources & evidence

ORD record
ord-730e4c9d6dce449d8560c126f40071e2
Source dataset
uspto-grants-2015_08
Patent number
US09101616B2

Reaction notes

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