HCID 86604966, compound → HCID 68505502, compound

HRID 1714034Notes

Reaction equation

HRID 1714034 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:28]([O:30][CH3:31])=[O:29])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:19]=2[O:18][CH2:17][C@@H:16]([OH:27])[CH2:15]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)Cl.CCOC(C)=O>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:28]([O:30][CH3:31])=[O:29])=[CH:12][C:13]=3[N:14]3[C:21]=2[C:20]2[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:19]=2[O:18][CH2:17][C:16](=[O:27])[CH2:15]3)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 86604966HCID 86604966, compound

Product 1

HCID 68505502HCID 68505502, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the foregoing alcohol (from Step 3) in DCM (0.06 M) was added DMP (1.5 eq.), and the mixture was stirred overnight at RT. The reaction mixture was diluted with EtOAc and washed with a 1:1 (v/v) mixture of sodium thiosulfate and sodium hydrogen carbonate (both saturated aqueous solutions), then with brine. Drying over Na2SO4, filtration and concentration i. vac. gave the crude product, which was used without further purification (92%); MS (ES+) m/z 422 (M+H)+.

Workup

  1. washwashed with a 1:1 (v/v) mixture of sodium thiosulfate and sodium hydrogen carbonate (both saturated aqueous solutions), then with brine
  2. dry with materialDrying over Na2SO4, filtration and concentration i

Sources & evidence

ORD record
ord-48adbf18edc4423d92c8f1e01493a181
Source dataset
uspto-grants-2010_09
Patent number
US07795247B2

Reaction notes

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