Sodium Bicarbonate → HCID 68456693, compound

HRID 2356843Notes

Reaction equation

HRID 2356843 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([C:20]2[CH:24]=[C:23]([NH:25][C:26](=[O:40])[CH:27]([NH:29][C:30]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[O:31])[CH3:28])[N:22]([C:41]([CH3:44])([CH3:43])[CH3:42])[N:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.C([O-])(O)=O.[Na+]>FC(F)(F)C(O)=O>[CH2:33]([O:32][C:30](=[O:31])[NH:29][CH:27]([C:26](=[O:40])[NH:25][C:23]1[N:22]([C:41]([CH3:43])([CH3:42])[CH3:44])[N:21]=[C:20]([C:11]2([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH:24]=1)[CH3:28])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 68455930HCID 68455930, compound

Product 1

HCID 68456693HCID 68456693, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 0.54 g (0.9 mmol) of 4-[5-(2-benzyloxycarbonylamino-propionylamino)-1-tert-butyl-1H-pyrazol-3-yl]-4-phenylpiperidine-1-carboxylic acid tert-butyl ester in 4.0 mL of neat trifluoroacetic acid was stirred at rt for 15 min. The reaction mixture was then poured into sat. aq. NaHCO3 and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated to afford {1-[2-tert-butyl-5-(4-phenylpiperidin-4-yl)-2H-pyrazol-3-ylcarbamoyl]ethyl}-carbamic acid benzyl ester which was used without further purification.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5c07761954cd459e8a3e17dfe173b26f
Source dataset
uspto-grants-2010_07
Patent number
US07759382B2

Reaction notes

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