Potassium tert-butoxide → 5-[4-(Difluoromethoxy)phenyl]-1-[(1-oxidothiomorpholin-4-yl)carbonyl]piperidine-3-carboxylic acid

HRID 220036Notes

Reaction equation

HRID 220036 reaction equation
[F:1][CH:2]([F:29])[O:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][N:14]([C:16]([N:18]3[CH2:23][CH2:22][S:21](=[O:24])[CH2:20][CH2:19]3)=[O:17])[CH2:13][CH:12]([C:25]([O:27]C)=[O:26])[CH2:11]2)=[CH:6][CH:5]=1.CC(C)([O-])C.[K+]>>[F:29][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([CH:10]2[CH2:15][N:14]([C:16]([N:18]3[CH2:23][CH2:22][S:21](=[O:24])[CH2:20][CH2:19]3)=[O:17])[CH2:13][CH:12]([C:25]([OH:27])=[O:26])[CH2:11]2)=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 58116576Methyl 5-[4-(difluoromethoxy)phenyl]-1-[(1-oxidothiomorpholin-4-yl)carbonyl]piperidine-3-carboxylate

Product 1

HCID 581165795-[4-(Difluoromethoxy)phenyl]-1-[(1-oxidothiomorpholin-4-yl)carbonyl]piperidine-3-carboxylic acid

Procedure

According to General Method 4A, 2.7 g (6.3 mmol) of methyl 5-[4-(difluoromethoxy)phenyl]-1-[(1-oxidothiomorpholin-4-yl)carbonyl]piperidine-3-carboxylate were reacted with 7.1 g (63.3 mmol) of potassium tert-butoxide. The reaction mixture was concentrated under reduced pressure, and the residue was suspended in water and acidified with concentrated hydrochloric acid. The precipitate was filtered off, washed with water and dried under reduced pressure. Yield: 1.1 g (34% of theory)

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-b3d6a06184774f278bfe5d9c96cfc75e
Source dataset
uspto-grants-2012_06
Patent number
US08202862B2

Reaction notes

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