Bromocyclopentane → HCID 178493633, compound

HRID 1944750Notes

Reaction equation

HRID 1944750 reaction equation
[CH:1]1(Br)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]([NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([NH:25][S:26]([C:29]3[CH:34]=[CH:33][C:32]([OH:35])=[C:31]([O:36][CH3:37])[CH:30]=3)(=[O:28])=[O:27])[CH2:21][CH2:20]2)=[O:18])[CH3:15])=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[F:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]([NH:16][C:17]([C@H:19]2[CH2:24][CH2:23][C@H:22]([NH:25][S:26]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)=[C:31]([O:36][CH3:37])[CH:30]=3)(=[O:28])=[O:27])[CH2:21][CH2:20]2)=[O:18])[CH3:15])=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 8728BromocyclopentaneHCID 11430Potassium CarbonateHCID 178493632HCID 178493632, compound

Product 1

HCID 178493633HCID 178493633, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

Cyclopentylbromide (10.45 mg, 0.07 mmol) was added to solution of trans-4-(4-hydroxy-3-methoxy-benzenesulfonylamino)-cyclohexanecarboxylic acid [(R)-1-(4-fluoro-phenyl)-ethyl]-amide (Example 2, 31.6 mg, 0.07 mmol) and potassium carbonate (19.4 mg, 0.14 mmol) in dimethylformamide (700 ul). The reaction was heated 50° C. for 16 h, cooled to room temperature, diluted with ethyl acetate and rinsed with 1:1 water:brine. The organic layer was concentrated and purified by reverse-phase chromatography followed by lyophilization to yield title compound (18 mg, 0.035 mmol). MS MH+ 519.1

Workup

  1. temperaturecooled to room temperature
  2. washrinsed with 1:1 water
  3. concentrationThe organic layer was concentrated
  4. custompurified by reverse-phase chromatography

Sources & evidence

ORD record
ord-14270bebb7f443d19e328d52547fc536
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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