Pyridine → HCID 58181624, compound

HRID 876589Notes

Reaction equation

HRID 876589 reaction equation
[OH:1][C@H:2]([C@H:10]1[O:15][CH2:14][CH2:13][N:12]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[CH2:21][N:20]([CH3:25])[C:19]3=[O:26])[C:11]1=[O:27])[C:3]([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4].N1C=CC=CC=1.[CH3:34][C:35](OC(C)=O)=[O:36]>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:35]([O:1][C@H:2]([C@H:10]1[O:15][CH2:14][CH2:13][N:12]([C:16]2[CH:17]=[C:18]3[C:22](=[CH:23][CH:24]=2)[CH2:21][N:20]([CH3:25])[C:19]3=[O:26])[C:11]1=[O:27])[C:3]([O:5][C:6]([CH3:8])([CH3:9])[CH3:7])=[O:4])(=[O:36])[CH3:34]

Participants

7

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 581819301,1-Dimethylethyl (αR,2R)-4-(2,3-dihydro-2-methyl-3-oxo-1H-isoindol-5-yl)-α-hydroxy-3-oxo-2-morpholineacetate

Product 1

HCID 58181624HCID 58181624, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 70-2 (80 mg) in CH2Cl2 (2 ml) at 0° C. was added pyridine (26 μL), Ac2O (30 μl), and DMAP (4 mg). The mixture was stirred for 1 hour at 0° C., warmed to rt, and stirred for an additional 12 h. The mixture was diluted with EtOAc and the organic layer was washed sequentially with sat. aq. CuSO4 solution, water, and brine. The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure to afford compound 70-3 (85 mg) as a light yellow semisolid. LC-MS: M+H=419. This material was used without further purification.

Workup

  1. temperaturewarmed to rt
  2. stirringstirred for an additional 12 h
  3. washthe organic layer was washed sequentially with sat. aq. CuSO4 solution, water, and brine
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4eb7c4476c1748c5ae69e811a0adc760
Source dataset
uspto-grants-2015_03
Patent number
US08987242B2

Reaction notes

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