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

HRID 661225Notes

Reaction equation

HRID 661225 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-f90ec0fee40b45c3863ab5b0c8392287
Source dataset
uspto-grants-2011_12
Patent number
US08084469B2

Reaction notes

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