Methanol → HCID 86692176, compound

HRID 1525144Notes

Reaction equation

HRID 1525144 reaction equation
[OH:1][CH2:2][C@@H:3]1[CH2:8][N:7]([C:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:6][C@H:5]([N:28]2[CH:33]=[CH:32][C:31]([NH:34][C:35](=[O:42])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)=[N:30][C:29]2=[O:43])[O:4]1.[C:44]1(=[O:50])[O:49][C:47](=[O:48])[CH2:46][CH2:45]1.CO>CN(C)C1C=CN=CC=1.ClCCl>[C:35]([NH:34][C:31]1[CH:32]=[CH:33][N:28]([C@H:5]2[CH2:6][N:7]([C:9]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:8][C@@H:3]([CH2:2][O:1][C:44](=[O:50])[CH2:45][CH2:46][C:47]([OH:49])=[O:48])[O:4]2)[C:29](=[O:43])[N:30]=1)(=[O:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 7922Succinic anhydrideHCID 16662128Benzamide, N-(1,2-dihydro-1-(6-(hydroxymethyl)-4-(triphenylmethyl)-2-morpholinyl)-2-oxo-4-pyrimidinyl)-, (2R-cis)-

Product 1

HCID 86692176HCID 86692176, compoundYield 100.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

Under argon atmosphere, 22.0 g of N-{1-[(2R,6S)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}benzamide and 7.04 g of 4-dimethylaminopyridine (4-DMAP) were suspended in 269 mL of dichloromethane, and 5.76 g of succinic anhydride was added to the suspension, followed by stirring at room temperature for 3 hours. To the reaction solution was added 40 mL of methanol, and the mixture was concentrated under reduced pressure. The residue was extracted using ethyl acetate and 0.5M aqueous potassium dihydrogenphosphate solution. The resulting organic layer was washed sequentially with 0.5M aqueous potassium dihydrogenphosphate solution, water and brine in the order mentioned. The resulting organic layer was dried over sodium sulfate and concentrated under reduced pressure to give 25.9 g of the product.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. extractionThe residue was extracted
  3. washThe resulting organic layer was washed sequentially with 0.5M aqueous potassium dihydrogenphosphate solution, water and brine in the order
  4. dry with materialThe resulting organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-f188b47de2954a5bb2b7d7df4f1fd207
Source dataset
uspto-grants-2015_07
Patent number
US09079934B2

Reaction notes

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