Hydrochloric Acid → HCID 22843232, compound

HRID 1029926Notes

Reaction equation

HRID 1029926 reaction equation
C([O:4][C@@H:5]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:6]([N:8]1[CH2:16][C@H:15]2[C@H:10]([C:11]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][CH2:13][C:14]2=[O:17])[CH2:9]1)=[O:7])(=O)C.[OH-].[Na+].Cl>O.C(O)C.C(OCC)(=O)C>[OH:4][C@@H:5]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:6]([N:8]1[CH2:16][C@H:15]2[C@H:10]([C:11]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:12][CH2:13][C:14]2=[O:17])[CH2:9]1)=[O:7]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22843228HCID 22843228, compound

Product 1

HCID 22843232HCID 22843232, compoundYield 71.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of (3aR,7aR)-2-[(S)-2-acetoxy-2-phenylacetyl]-7,7-diphenyl-4-perhydroisoindolone (2 g) in a mixture of water (20 cc) and ethanol (25 cc) is treated with normal sodium hydroxide solution (5 cc) and the mixture is refluxed for 1 hour, then diluted with water (100 cc) and ethyl acetate (50 cc) and neutralized by the addition of normal hydrochloric acid (5 cc). The organic phase is washed with water (50 cc) and with a saturated sodium chloride solution (50 cc), dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa) to give (3aR,7aR)-2-[(S)-2-hydroxy-2-phenylacetyl]-7,7-diphenyl-4-perhydroisoindolone (1.3 g) in the form of a white meringue.

Workup

  1. temperaturethe mixture is refluxed for 1 hour
  2. washThe organic phase is washed with water (50 cc) and with a saturated sodium chloride solution (50 cc)
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)

Sources & evidence

ORD record
ord-ef6c9708a07c4dfda930afef01637e24
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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