Hydrochloric Acid → HCID 67754949, compound

HRID 1609504Notes

Reaction equation

HRID 1609504 reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH:5]([N:10]([CH2:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:28])[CH:22]=[CH:21]2)=[O:12])[C:6](OC)=O.B.[Na].Cl.C([OH:41])C>>[CH3:1][S:2][CH2:3][CH2:4][C:5]([CH3:6])([N:10]([CH2:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:28])[CH:22]=[CH:21]2)=[O:12])[OH:41]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14747788HCID 14747788, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 67754949HCID 67754949, compound

Procedure

In 80 ml of ethanol is dissolved 1.6 g of 6-{4-[N-(3-methylthio-1-methoxycarbonylpropyl)-N-cyclohexylmethylaminocarbonyl]butoxy}carbostyril. Thereto is added 3.2 g of sodium boron hydride. The mixture is stirred for 2 hours at 50°-60° C. The reaction mixture is neutralized with diluted hydrochloric acid and concentrated. The residue is extracted with a mixture of chloroform and methanol (10:1). The extract is purified by means of a silica gel column chromatography (eluant; chloroform:methanol=20:1). The resulting residue is recrystallized from a mixed solvent of dichloromethane-ethyl acetate-diethyl ether to obtain 0.78 g of 6-{4-[N-(3-methylthio-1-hydroxy-methylpropyl)-N-cyclohexylmethylaminocarbonyl]butoxy}carbostyril.

Workup

  1. concentrationconcentrated
  2. extractionThe residue is extracted with a mixture of chloroform and methanol (10:1)
  3. customThe extract is purified by means of a silica gel column chromatography (eluant; chloroform:methanol=20:1)
  4. customThe resulting residue is recrystallized from a mixed solvent of dichloromethane-ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-43246cc16932481e985bd54a7818bc2d
Source dataset
uspto-grants-1995_03
Patent number
US05401740

Reaction notes

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