Hydrochloric Acid → (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-(3-indolyl)acetylperhydroisoindole-4,5-diol

HRID 375446Notes

Reaction equation

HRID 375446 reaction equation
CN(C)CCCN=C=NCC.C(NC(C)C)(C)C.Cl.[C:20]1([C:26]2([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH:34]3[CH:30]([CH2:31][NH:32][CH2:33]3)[C:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[O:42][CH3:43])([OH:35])[CH:28]([OH:44])[CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[NH:51]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[C:53]([CH2:60][C:61](O)=[O:62])=[CH:52]1.Cl.[Cl-].[Na+]>ClCCl.O.ON1C2C=CC=CC=2N=N1>[C:45]1([C:26]2([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:34]3[CH:30]([CH2:31][NH:32][CH:33]3[C:61](=[O:62])[CH2:60][C:53]3[C:54]4[C:59](=[CH:58][CH:57]=[CH:56][CH:55]=4)[NH:51][CH:52]=3)[C:29]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[O:42][CH3:43])([OH:35])[CH:28]([OH:44])[CH2:27]2)[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 802Indole-3-Acetic AcidHCID 5234Sodium ChlorideHCID 7912DiisopropylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 677192977,7-Diphenyl-4-(2-methoxyphenyl)-perhydroisoindole-4,5-diol hydrochloride

Product 1

HCID 67736917(3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-(3-indolyl)acetylperhydroisoindole-4,5-diolYield 74.5%

Reagents, catalysts & solvents 2

HCID 27960291-Hydroxybenzotriazole hydrateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

0.46 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and 0.34 cm3 of diisopropylamine are added to a solution of 0.9 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)perhydroisoindole-4,5-diol hydrochloride, 0.4 g of 3-indolylacetic acid and 20 mg of 1-hydroxybenzotriazole hydrate in 90 cm3 of dichloromethane, cooled to 0° C. The mixture is stirred at room temperature for 15 hours, acidified with 0.1N HCl and then taken up in an aqueous saturated solution of sodium chloride. The organic phase is decanted, dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The foam obtained is recrystallized from 10 cm3 of boiling acetonitrile. 0.85 g of (3aRS,4RS,5RS,7aRS)-7,7-diphenyl-4-(2-methoxyphenyl)-2-(3-indolyl)acetylperhydroisoindole-4,5-diol is obtained in the form of a white solid which melts at 266° C.

Workup

  1. customThe organic phase is decanted
  2. dry with materialdried over magnesium sulphate
  3. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  4. customThe foam obtained
  5. customis recrystallized from 10 cm3 of boiling acetonitrile

Sources & evidence

ORD record
ord-b3c8507219ae48fcbd3eb9ef6a81214a
Source dataset
uspto-grants-1996_01
Patent number
US05484804

Reaction notes

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