Trifluoroacetic acid → HCID 66999727, compound

HRID 559311Notes

Reaction equation

HRID 559311 reaction equation
C(O[C:6](=O)[N:7]([CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([N:17]2[CH2:21][CH:20]([C:22]3[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=3)[CH:19]([CH:30]([O:32][C:33]3[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][N:34]=3)[CH3:31])[CH2:18]2)=[O:16])[CH2:11][CH2:10]1)C)(C)(C)C.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:29][C:24]1[CH:23]=[C:22]([CH:20]2[CH2:21][N:17]([C:15]([CH:12]3[CH2:13][CH2:14][CH:9]([NH:7][CH3:6])[CH2:10][CH2:11]3)=[O:16])[CH2:18][CH:19]2[CH:30]([O:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][N:34]=2)[CH3:31])[CH:27]=[CH:26][C:25]=1[Cl:28]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 66999195HCID 66999195, compound

Product 1

HCID 66999727HCID 66999727, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of {4-[(3RS,4SR)-3-[(SR)-1-(5-cyano-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl]-cyclohexyl}-methyl-carbamic acid tert-butyl ester described herein above (30 mg, 0.050 mmol) in CH2Cl2 (4 mL) was added TFA (1 mL). After 1 hour, aqueous NaHCO3 was added until ph=8, the product was extracted with CH2Cl2. The combined organic phases were dried over Na2SO4 to give the title product as a colorless oil (25 mg, 98%). ES-MS m/e: 500.9 (M+H+).

Workup

  1. extractionthe product was extracted with CH2Cl2
  2. dry with materialThe combined organic phases were dried over Na2SO4

Sources & evidence

ORD record
ord-6e384da02c5e497a8bf9c3ac48e2c79b
Source dataset
uspto-grants-2011_11
Patent number
US08063075B2

Reaction notes

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