Water → 4-(2-Isopropoxy-3-methyl-benzoylamino)-tetrahydro-thiopyran-4-carboxylic acid

HRID 1047686Notes

Reaction equation

HRID 1047686 reaction equation
C[O:2][C:3]([C:5]1([NH:11][C:12](=[O:24])[C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:14]=2[O:20][CH:21]([CH3:23])[CH3:22])[CH2:10][CH2:9][S:8][CH2:7][CH2:6]1)=[O:4].[OH-].[K+].O>CCO>[CH:21]([O:20][C:14]1[C:15]([CH3:19])=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]([NH:11][C:5]1([C:3]([OH:4])=[O:2])[CH2:6][CH2:7][S:8][CH2:9][CH2:10]1)=[O:24])([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 593141894-(2-Isopropoxy-3-methyl-benzoylamino)-tetrahydro-thiopyran-4-carboxylic acid methyl ester

Product 1

HCID 593141484-(2-Isopropoxy-3-methyl-benzoylamino)-tetrahydro-thiopyran-4-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of 4-(2-isopropoxy-3-methyl-benzoylamino)-tetrahydro-thiopyran-4-carboxylic acid methyl ester (28) (75 mg, 0.21 mmol) and KOH (500 mg, 8.9 mmol) is dissolved in EtOH (5 mL) and water (0.5 mL) under a water bath. The water bath is removed when KOH is completely dissolved and the resulting reaction solution is stirred at RT for 8 h. After concentration in vacuo, the residue is dissolved in water (20 mL) and acidified with conc. HCl until no more precipitate came out of the water. The precipitate is filtered to give a pure product (29) as a pale yellow solid (68 mg, 94%).

Workup

  1. customThe water bath is removed when KOH
  2. dissolutionis completely dissolved
  3. customthe resulting reaction solution
  4. concentrationAfter concentration in vacuo
  5. dissolutionthe residue is dissolved in water (20 mL)
  6. filtrationThe precipitate is filtered

Sources & evidence

ORD record
ord-4405809c70764717a31f95d8098d0567
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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