Ammonium Chloride → HCID 59272306, compound

HRID 1970258Notes

Reaction equation

HRID 1970258 reaction equation
[BH4-].[Na+].[NH2:3][C:4]1[O:5][CH2:6][C@@:7]2([N:34]=1)[C:20]1[CH:19]=[C:18]([C:21](=[O:27])[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:17]=[CH:16][C:15]=1[O:14][C:13]1[C:8]2=[CH:9][C:10]([C:28]2[CH:29]=[N:30][CH:31]=[N:32][CH:33]=2)=[CH:11][CH:12]=1.[Cl-].[NH4+]>CO.C(OCC)(=O)C.O>[NH2:3][C:4]1[O:5][CH2:6][C@@:7]2([N:34]=1)[C:20]1[CH:19]=[C:18]([CH:21]([OH:27])[CH2:22][C:23]([CH3:25])([CH3:26])[CH3:24])[CH:17]=[CH:16][C:15]=1[O:14][C:13]1[C:8]2=[CH:9][C:10]([C:28]2[CH:29]=[N:30][CH:31]=[N:32][CH:33]=2)=[CH:11][CH:12]=1

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 59272309HCID 59272309, compound

Product 1

HCID 59272306HCID 59272306, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium borohydride (33.1 mg, 874 μmol) was added at RT to a solution of 1-((4S)-2-amino-7′-(5-pyrimidinyl)spiro[1,3-oxazole-4,9′-xanthen]-2′-yl)-3,3-dimethyl-1-butanone (312 mg, 728 μmol) in methanol (5 ml) and the mixture was stirred for 1 hr at ambient temperature. Saturated ammonium chloride solution (3 ml) was added, the mixture was diluted with ethyl acetate (5 ml) and water was added to dissolve solids. The organic layer was washed with brine, dried and concentrated to give pink solid which was purified by chromatography on silica gel (12 g Redi-Sep column, 15-75% DCM/MeOH/NH4OH 90:10:1 in DCM) to afford (1RS)-1-((4S)-2-amino-7′-(5-pyrimidinyl)spiro[1,3-oxazole-4,9′-xanthen]-2′-yl)-3,3-dimethyl-1-butanol as white solid.

Workup

  1. additionwas added
  2. dissolutionto dissolve solids
  3. washThe organic layer was washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customto give pink solid which
  7. customwas purified by chromatography on silica gel (12 g Redi-Sep column, 15-75% DCM/MeOH/NH4OH 90:10:1 in DCM)

Sources & evidence

ORD record
ord-1b6d431869794e93b494e19e67c33dcc
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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