Chloroform → HCID 14891481, compound

HRID 466370Notes

Reaction equation

HRID 466370 reaction equation
Cl.[CH2:2]([N:4]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1)=[O:8])[CH3:3].[BH4-].[Na+].C(Cl)(Cl)Cl>C(O)C.C(Cl)(Cl)(Cl)Cl>[CH2:2]([N:4]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])=[CH:11][CH:10]=1)[OH:8])[CH3:3]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 67895011HCID 67895011, compound

Product 1

HCID 14891481HCID 14891481, compound

Reagents, catalysts & solvents 1

HCID 23446399HCID 23446399, compoundSolvent

Procedure

The crude mixture containing N-[4-[3-(ethylheptylamino)-1-oxopropyl]phenyl]methanesulfonamide hydrochloride from Preparation 16 (1.0 g, 2.6 mmol) is transferred to a reaction flask in ethanol-carbon tetrachloride, concentrated, treated with benzene and concentrated again in vacuo. The residue in 18 ml of ethanol, under nitrogen, is cooled in an ice bath and treated with powdered NaBH4 (0.23 g, 0.006 mol) in portions (foaming) over 20 min. The mixture is stirred for 15 min in the cold and for 2.5 hrs at room temperature. It is then treated with 20 ml of ice-water in portions over 5 min. Chloroform (10 ml) is added to the resultant suspension; the mixture is stirred 5 min; and, the layers are separated. The aqueous phase is extracted with additional chloroform (3×50 ml). (Each extract is backwashed with 5 ml of H2O). The pooled organic extract is washed with brine, dried (Na2SO4) and concentrated to give 0.85 g of crude material (two main spots by TLC). This material is chromatographed over 250 ml of silica gel with 0.5% NH4OH/7.5% MeOH/CHCl3 ; 16 ml fractions are collected. Fractions at approximately 36-54 give the title compound which is crystallized from ether-pentane; m.p. 74°-75° C.

Workup

  1. concentrationconcentrated
  2. additiontreated with benzene
  3. concentrationconcentrated again in vacuo
  4. temperatureThe residue in 18 ml of ethanol, under nitrogen, is cooled in an ice bath
  5. stirringthe mixture is stirred 5 min
  6. customand, the layers are separated
  7. extractionThe aqueous phase is extracted with additional chloroform (3×50 ml)
  8. extractionThe pooled organic extract
  9. washis washed with brine
  10. dry with materialdried (Na2SO4)
  11. concentrationconcentrated
  12. customto give 0.85 g of crude material (two main spots by TLC)
  13. customThis material is chromatographed over 250 ml of silica gel with 0.5% NH4OH/7.5% MeOH/CHCl3
  14. custom16 ml fractions are collected

Sources & evidence

ORD record
ord-907dbe77af774dbea357ecda7348e2d4
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Reaction notes

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