Water → HCID 86600949, compound

HRID 747516Notes

Reaction equation

HRID 747516 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:15][CH2:16][CH2:17][N:18]1[C:22]([C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)=[CH:21][S:20][C:19]1=[N:30][C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][C:32]=1[O:38][CH3:39])[CH2:9][C:10](OCC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].O>O1CCCC1>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([N:30]=[C:19]2[N:18]([CH2:17][CH2:16][CH2:15][N:8]([CH2:9][CH2:10][OH:11])[C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:22]([C:23]3[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=3)=[CH:21][S:20]2)=[C:32]([O:38][CH3:39])[CH:33]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 22350969HCID 22350969, compound

Product 1

HCID 86600949HCID 86600949, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the compound (3 g) obtained in the above (1) in tetrahydrofuran (20 ml) was added lithium borohydride (170 mg), and the mixture was stirred at room temperature overnight. To the reaction mixture was added water, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated brine, dried over sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography [n-hexane:ethyl acetate (1:1)] to give the title compound (2.14 g) as amorphous.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated brine
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography [n-hexane:ethyl acetate (1:1)]

Sources & evidence

ORD record
ord-b31cd0f040894682a201e53af5d89622
Source dataset
uspto-grants-2008_07
Patent number
US07396842B2

Reaction notes

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