Sodium borohydride → HCID 59000916, compound

HRID 529186Notes

Reaction equation

HRID 529186 reaction equation
[F:1][C:2]1[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[C:3]=1[CH2:4][N:5]1[C:10]2[S:11][C:12]([C:21]3[CH:26]=[CH:25][C:24]([NH:27][C:28]([NH:30][O:31][CH3:32])=[O:29])=[CH:23][CH:22]=3)=[C:13]([CH2:14][N:15]([CH2:17][CH2:18][O:19][CH3:20])[CH3:16])[C:9]=2[C:8](=[O:33])[N:7]([CH2:34][C:35](=[O:40])[C:36]([CH3:39])([CH3:38])[CH3:37])[C:6]1=[O:41].[BH4-].[Na+]>CO.C1COCC1>[F:46][C:42]1[CH:43]=[CH:44][CH:45]=[C:2]([F:1])[C:3]=1[CH2:4][N:5]1[C:10]2[S:11][C:12]([C:21]3[CH:22]=[CH:23][C:24]([NH:27][C:28]([NH:30][O:31][CH3:32])=[O:29])=[CH:25][CH:26]=3)=[C:13]([CH2:14][N:15]([CH2:17][CH2:18][O:19][CH3:20])[CH3:16])[C:9]=2[C:8](=[O:33])[N:7]([CH2:34][CH:35]([OH:40])[C:36]([CH3:37])([CH3:38])[CH3:39])[C:6]1=[O:41]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59000864HCID 59000864, compound

Product 1

HCID 59000916HCID 59000916, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of compound (120 mg, 0.182 mmol) obtained in Example 63 in methanol (6 ml) and THF (4 ml) was added sodium borohydride (6.9 mg, 0.182 mmol) under ice cooling. The reaction liquid was stirred at room temperature for 1.5 hours and concentrated under reduced pressure. The residue was distributed between water and ethyl acetate, and the organic layer was extracted. The extract was washed with brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by NH-silica gel (Produced by Fuji Silysia Chemical Ltd.) column chromatography (eluent;ethyl acetate), and recrystallized from ethyl acetate and diethylether to give the title compound (81.1 mg, 68%) as colorless crystals.

Workup

  1. customThe reaction liquid
  2. concentrationconcentrated under reduced pressure
  3. extractionthe organic layer was extracted
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by NH-silica gel (Produced by Fuji Silysia Chemical Ltd.) column chromatography (eluent;ethyl acetate)
  8. customrecrystallized from ethyl acetate and diethylether

Sources & evidence

ORD record
ord-4502c53053bd486293fa0ef22ca68dd1
Source dataset
uspto-grants-2016_05
Patent number
US09346822B2

Reaction notes

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