Water → 1,1-Dimethylethyl 4-{carbamoyl[4-(2,2-difluoroethoxy)-2-(methoxycarbonyl)-phenyl]amino}piperidine-1-carboxylate

HRID 403559

Reaction equation

HRID 403559 reaction equation
[N-:1]=[C:2]=[O:3].[K+].O.[F:6][CH:7]([F:34])[CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:19][CH2:18]2)=[C:12]([C:30]([O:32][CH3:33])=[O:31])[CH:11]=1>CC(O)=O>[C:2]([N:16]([C:13]1[CH:14]=[CH:15][C:10]([O:9][CH2:8][CH:7]([F:34])[F:6])=[CH:11][C:12]=1[C:30]([O:32][CH3:33])=[O:31])[CH:17]1[CH2:18][CH2:19][N:20]([C:23]([O:25][C:26]([CH3:28])([CH3:29])[CH3:27])=[O:24])[CH2:21][CH2:22]1)(=[O:3])[NH2:1]

Participants

5

Reactant 3

HCID 962WaterHCID 11051572Potassio isocyanateHCID 595871981,1-Dimethylethyl 4-{[4-(2,2-difluoroethoxy)-2-(methoxycarbonyl)phenyl]amino}piperidine-1-carboxylate

Product 1

HCID 595872271,1-Dimethylethyl 4-{carbamoyl[4-(2,2-difluoroethoxy)-2-(methoxycarbonyl)-phenyl]amino}piperidine-1-carboxylateYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1.95 g of potassium isocyanate in solution of 4 ml of water are added to a solution of 6.63 g of 1,1-dimethylethyl 4-{[4-(2,2-difluoroethoxy)-2-(methoxycarbonyl)phenyl]amino}piperidine-1-carboxylate obtained in stage 3.3 in 40 ml of AcOH. The mixture is stirred at AT for 12 h 00. It is extracted with AcOEt and the extract is washed with a saturated K2CO3 solution and then with water. It is dried over MgSO4, filtered and evaporated under reduced pressure to give 6.95 g of the expected product.

Workup

  1. extractionIt is extracted with AcOEt
  2. washthe extract is washed with a saturated K2CO3 solution
  3. dry with materialIt is dried over MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-a0803f8deb05472087a0aa8fe6d2dc05
Source dataset
uspto-grants-2014_06
Patent number
US08748441B2

Linked notes

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