Hydrochloric Acid → HCID 67915940, compound

HRID 1029897Notes

Reaction equation

HRID 1029897 reaction equation
C(OC([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([N:18]1[CH2:26][CH:25]2[CH:20]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:22][CH2:23][C:24]2=[O:27])[CH2:19]1)=[O:17])=O)(C)(C)C.[ClH:40]>O1CCOCC1>[ClH:40].[NH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16]([N:18]1[CH2:26][CH:25]2[CH:20]([C:21]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH2:22][CH2:23][C:24]2=[O:27])[CH2:19]1)=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67915859HCID 67915859, compound

Product 1

HCID 67915940HCID 67915940, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(3aRS,7aRS)-2-[(2-tert-butoxycarbonylaminophenyl)acetyl]-7,7-diphenyl-4-perhydroisoindolone (1.5 g) is treated with a 5.7N solution (15 cc) of hydrochloric acid in dry dioxane at 20° C. for 4 hours. The reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa) and the residue is purified by dissolving in acetonitrile (20 cc) and precipitating from isopropyl ether (30 cc). The solid is drained, washed with isopropyl ether and dried. (3aRS,7aRS)-2-[(2-aminophenyl)acetyl]-7,7-diphenyl-4-perhydroisoindolone hydrochloride (1.1 g) is obtained in the form of a slightly pink solid.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness under reduced pressure (2.7 kPa)
  2. customthe residue is purified
  3. dissolutionby dissolving in acetonitrile (20 cc)
  4. customprecipitating from isopropyl ether (30 cc)
  5. washwashed with isopropyl ether
  6. customdried

Sources & evidence

ORD record
ord-da2961e9a8f84bef83b7a270b176f477
Source dataset
uspto-grants-1992_04
Patent number
US05102667

Reaction notes

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