Dimethylformamide → HCID 67264883, compound

HRID 1685187Notes

Reaction equation

HRID 1685187 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14](=O)[N:15]([C@@H:30]2[CH2:35][CH2:34][CH2:33][N:32]([C:36]([O:38][CH2:39][C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)=[O:37])[CH2:31]2)[CH2:16][C:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]([C:26]([F:29])([F:28])[F:27])[CH:20]=2)=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C[N:48](C=O)C>C([O-])(=O)C.[NH4+].C(O)(=O)C.CC(=O)OCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[N:15]([C@@H:30]3[CH2:35][CH2:34][CH2:33][N:32]([C:36]([O:38][CH2:39][C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)=[O:37])[CH2:31]3)[CH:16]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[C:21]([C:26]([F:27])([F:29])[F:28])[CH:20]=3)[N:48]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 67264998HCID 67264998, compound

Product 1

HCID 67264883HCID 67264883, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolventHCID 517165Ammonium AcetateSolvent

Procedure

Heat a solution of 4-{((R)-1-benzyloxycarbonyl-piperidin-3-yl)-[2-(4-fluoro-3-trifluoromethyl-phenyl)-2-oxo-ethyl]-carbamoyl}-piperidine-1-carboxylic acid tert-butyl ester (4.40 mmol; 2.86 g) in DMF (2.5 mL) and ammonium acetate saturated in acetic acid (15 mL) at 90° C. for 8 h. Dilute with EA, wash the organic phase 3× with water, saturated sodium bicarbonate, brine, dry over MgSO4 and filter. Purify the residue on 80 g silica gel with 5-20% EA/DCM to provide the title compound (2.08 g; 3.30 mmol; 75%). MS (ES+): m/z=631 (M+H).

Workup

  1. washwash the organic phase 3× with water, saturated sodium bicarbonate, brine
  2. dry with materialdry over MgSO4
  3. filtrationfilter
  4. customPurify the residue on 80 g silica gel with 5-20% EA/DCM

Sources & evidence

ORD record
ord-1e6d261bea3e436ebb18c7d4f6ee9ea0
Source dataset
uspto-grants-2012_04
Patent number
US08148387B2

Reaction notes

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