Tetrahydrofuran → HCID 86731351, compound

HRID 2277272Notes

Reaction equation

HRID 2277272 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([C:14]2[O:15][C:16]3[CH:22]=[C:21]([O:23][CH2:24][C@@H:25]([NH:27][C:28](=[O:30])[CH3:29])[CH3:26])[CH:20]=[CH:19][C:17]=3[N:18]=2)[CH:7]=[C:8]([F:13])[C:9]=1[O:10][CH2:11][CH3:12])(=[O:3])[CH3:2].C1COCC1.[BH4-].[Na+].[Cl-].[NH4+]>C(OCC)(=O)C.CO>[CH2:11]([O:10][C:9]1[C:4]([CH:1]([OH:3])[CH3:2])=[CH:5][C:6]([C:14]2[O:15][C:16]3[CH:22]=[C:21]([O:23][CH2:24][C@@H:25]([NH:27][C:28](=[O:30])[CH3:29])[CH3:26])[CH:20]=[CH:19][C:17]=3[N:18]=2)=[CH:7][C:8]=1[F:13])[CH3:12]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86731349HCID 86731349, compound

Product 1

HCID 86731351HCID 86731351, compoundYield 63.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of N-((2S)-1-((2-(3-acetyl-4-ethoxy-5-fluorophenyl)-1,3-benzoxazol-6-yl)oxy)propan-2-yl)acetamide (660 mg), THF (10 mL) and methanol (5 mL) was added sodium borohydride (60.3 mg), and the mixture was stirred at room temperature for 10 min. To the reaction mixture was added saturated aqueous ammonium chloride solution, and the mixture was diluted with ethyl acetate, and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate-ethyl acetate/methanol) to give the title compound (420 mg).

Workup

  1. dry with materialdried over anhydrous magnesium sulfate
  2. customThe solvent was evaporated
  3. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate-ethyl acetate/methanol)

Sources & evidence

ORD record
ord-e3114e8ac6c64316b4c6b9efd1357331
Source dataset
uspto-grants-2015_09
Patent number
US09133129B2

Reaction notes

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