Acetic Anhydride → HCID 20027815, compound

HRID 1722862Notes

Reaction equation

HRID 1722862 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]23[CH2:21][CH:19]([CH2:20]2)[C:18](=[O:22])[N:17]([CH2:23][CH2:24][CH3:25])[C:16]3=[O:26])=[CH:11][CH:10]=1>O1CCCC1.CN(C)C1C=CN=CC=1.C(O)C>[C:1]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]23[CH2:20][CH:19]([CH2:21]2)[C:18](=[O:22])[N:17]([CH2:23][CH2:24][CH3:25])[C:16]3=[O:26])=[CH:13][CH:14]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 148726221-(4-Amino-phenyl)-3-propyl-3-aza-bicyclo[3.1.1]heptane-2,4-dione

Product 1

HCID 20027815HCID 20027815, compound

Reagents, catalysts & solvents 3

HCID 702EthanolCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.11 ml of acetic anhydride in 0.5 ml of tetrahydrofuran is added dropwise to a solution of 260 mg of 1-(4-aminophenyl)-3-n-propyl-3-azabicyclo[3.1.1]heptane-2,4-dione and 6 mg of 4-dimethylaminopyridine in 8 ml of tetrahydrofuran. After stirring at room temperature for 21/2 hours, two drops of ethanol are added to the reaction mixture and stirring is continued for a further 15 minutes. After concentration by evaporation and subsequent recrystallisation from ethyl acetate/petroleum ether, the title compound is obtained in the form of white crystals having a melting point of 138.5°-139.5°. Rf (methylene chloride/methanol/glacial acetic acid 40:5:1)=0.55.

Workup

  1. additionare added to the reaction mixture
  2. concentrationAfter concentration
  3. customby evaporation and subsequent recrystallisation from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-06aa9c2d2a234e4fb54e5f1470171af4
Source dataset
uspto-grants-1989_08
Patent number
US04857660

Reaction notes

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