Methanol → HCID 131719493, compound

HRID 1078092Notes

Reaction equation

HRID 1078092 reaction equation
[O:1]1[CH2:5][CH2:4]CC1.[CH2:6]([NH:10][S:11]([CH2:14][CH:15]([OH:34])[CH:16]([OH:33])[CH:17]([NH:25][C:26](=O)[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)(=[O:13])=[O:12])[CH2:7][CH2:8][CH3:9].CO>C(Cl)(Cl)Cl>[C:5]([OH:1])(=[O:12])[CH3:4].[CH2:6]([NH:10][S:11]([CH2:14][CH:15]([OH:34])[CH:16]([OH:33])[CH:17]([NH:25][CH2:26][CH2:27][CH2:28][CH:29]([CH3:30])[CH3:31])[CH2:18][CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1)(=[O:12])=[O:13])[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 887Methanol2×HCID 8028TetrahydrofuranHCID 54378972HCID 54378972, compound

Product 1

HCID 131719493HCID 131719493, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Borane dimethylsulfide complex (10 molar, 0.9 ml., 9 mmole) was added dropwise to a tetrahydrofuran solution (3 ml.) of [1S-(1R*,2S*,3S*)]-N-[4-[(butylamino)sulfonyl]-1-(cyclohexylmethyl)-2,3-dihydroxybutyl]-4-methylpentanamide (100 mg., 0.23 mmole, product of Example 38). The reaction mixture is stirred at 50° for one hour, quenched with 1N HCl (10 ml.), and after 30 minutes, saturated sodium bicarbonate was added (pH 8). The product was extracted with ethyl acetate (2×150 ml.) and this solution was washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The resulting crude product was purified by chromatography through silica gel (20 g., Merck) using (2.5:0.1:100) methanol:acetic acid:chloroform. The appropriate fractions were combined and concentrated to yield 63 mg. of glassy, very hygroscopic white solid [βR-(βR*,γR*,δS*)]-N-butyl-β, γ-dihydroxy-δ-[(4-methylpentyl)amino]cyclohexanepentanesulfonamide, monoacetate salt; m.p. 68°-82°, [α]D =+14° (c=0 5, methanol). TLC (silica gel, methanol:chloroform, 1:9) Rf =0.46.

Workup

  1. customquenched with 1N HCl (10 ml.)
  2. waitafter 30 minutes
  3. additionsaturated sodium bicarbonate was added (pH 8)
  4. extractionThe product was extracted with ethyl acetate (2×150 ml.)
  5. washthis solution was washed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting crude product was purified by chromatography through silica gel (20 g., Merck)
  10. concentrationconcentrated
  11. customto yield 63 mg

Sources & evidence

ORD record
ord-70e6a052c2154f4b81eaf62e92616a07
Source dataset
uspto-grants-1996_08
Patent number
US05545838

Reaction notes

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