Water → HCID 67427009, compound

HRID 1925183Notes

Reaction equation

HRID 1925183 reaction equation
[CH2:1]([CH:3]([CH2:39][CH3:40])[CH2:4][C:5]1([C:11]([NH:13][C:14]2[C:15]([S:24]C(C3(CC(CC)CC)CCCCC3)=O)=[CH:16][C:17]3[C:22]([CH:23]=2)=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)[CH3:2].[OH-].[K+].O>CO.O1CCCC1>[SH:24][C:15]1[C:14]([NH:13][C:11]([C:5]2([CH2:4][CH:3]([CH2:39][CH3:40])[CH2:1][CH3:2])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]2)=[O:12])=[CH:23][C:22]2[C:17]([CH:16]=1)=[CH:18][CH:19]=[CH:20][CH:21]=2

Participants

6

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 86642989HCID 86642989, compound

Product 1

HCID 67427009HCID 67427009, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The crude product obtained in step A) is dissolved in a mixture of methanol and tetra-hydrofuran (1:1). Then 3.5 mol equivalents of potassium hydroxide are added at room temperature and the mixture is stirred for 1 hour. Then water is added and the mixture is washed with n-hexane. The aqueous layer is then acidified by addition of KHSO4 and extracted with chloroform. The combined extracts are washed with water and brine, dried (Na2SO4) and concentrated to obtain 1-(2-ethyl-butyl)-cyclohexanecarboxylic acid (3-mercapto-naphthalen-2-yl)-amide.

Workup

  1. washthe mixture is washed with n-hexane
  2. additionThe aqueous layer is then acidified by addition of KHSO4
  3. extractionextracted with chloroform
  4. washThe combined extracts are washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1b21271a842349d18c360f39d56ff149
Source dataset
uspto-grants-2012_05
Patent number
US08178583B2

Reaction notes

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