Hydrochloric Acid → HCID 67915940, compound

HRID 1196276Notes

Reaction equation

HRID 1196276 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-diphenylperhydro-4-isoindolone (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 purified by dissolution in acetonitrile (20 cc) and precipitation with isopropyl ether (30 cc). The solid is drained, washed with isopropyl ether and dried. (3aRS,7aRS)-2-[(2-Aminophenyl)acetyl]-7,7-diphenylperhydro-4-isoindolone hydrochloride (1.1 g) is obtained in the form of a slightly pinkish solid.

Workup

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

Sources & evidence

ORD record
ord-527941e20daa42b69c761d7da37b0632
Source dataset
uspto-grants-1992_05
Patent number
US05112988

Reaction notes

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