3-oxo-2,3-dihydro-1H-isoindole-1-carboxylic acid → 7-[(2,3-Dihydro-3-oxo-1H-isoindol-1-yl)carbonyl]-hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one

HRID 1713551Notes

Reaction equation

HRID 1713551 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([C:11]([OH:13])=O)[NH:3]1.[C:14]1([C:20]2([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:24]3[CH2:25][NH:26][CH2:27][CH2:28][N:23]3[C:22](=[O:29])[O:21]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(N(CC)CC)C>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]([C:11]([N:26]2[CH2:27][CH2:28][N:23]3[C:22](=[O:29])[O:21][C:20]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:24]3[CH2:25]2)=[O:13])[NH:3]1

Participants

4

Reactant 2

HCID 97940173-oxo-2,3-dihydro-1H-isoindole-1-carboxylic acidHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 231220377-[(2,3-Dihydro-3-oxo-1H-isoindol-1-yl)carbonyl]-hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-oneYield 14%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In the same manner as in Reference Example 19, the reaction was performed using 2,3-dihydro-3-oxo-1H-isoindole-1-carboxylic acid instead of 1,4-bis(phenylmethyl)-2-piperazine carboxylic acid, and using hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one instead of N,O-dimethylhydroxylamine hydrochloride and triethylamine. The reaction solution was extracted with ethyl acetate, washed with a 0.5 M aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To the residue was added hexane-ethyl acetate. Then, the obtained crystals were collected by filtration and washed with hexane to obtain the title compound. Yield 14%.

Workup

  1. extractionThe reaction solution was extracted with ethyl acetate
  2. washwashed with a 0.5 M aqueous sodium hydrogen carbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionTo the residue was added hexane-ethyl acetate
  6. filtrationThen, the obtained crystals were collected by filtration
  7. washwashed with hexane

Sources & evidence

ORD record
ord-cd76c4318a6c4a12b9cb90c45faa4751
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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