Methanol → HCID 21968352, compound

HRID 1106993Notes

Reaction equation

HRID 1106993 reaction equation
O.CO.[C:4]1([C@H:10]2[N:14]([NH:15][S:16]([C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[C@@H:13]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C@H:12]([C:34]([O:36]C)=[O:35])[O:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1>[C:4]1([C@H:10]2[N:14]([NH:15][S:16]([C:19]3[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=3)(=[O:18])=[O:17])[C@@H:13]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C@H:12]([C:34]([OH:36])=[O:35])[O:11]2)[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 11430Potassium CarbonateHCID 57298157HCID 57298157, compound

Product 1

HCID 21968352HCID 21968352, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Water (8 ml), methanol (8 ml) and THF (8 ml) are added to (2S,4S,5R)-2,4-diphenyl-3-(4-nitrobenzenesulfonamido)-5-methoxycarbonyl-1,3-oxazolidine (III, EXAMPLE 12A, 1.50 g 3.19 mmol). Potassium carbonate (1.018 g, 7.71 mmol) is then added. The resulting mixture is stirred at 20-25° until complete by TLC. After 5 hr the reaction is complete and the reaction mixture is extracted with basic methylene chloride (2×). The aqueous phase is then acidified with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate phase is then washed with water, saline and dried over magnesiuim sulfate. Concentration of the organic phase (ethyl acetate) gives the title compound, mp=61-65°.

Workup

  1. extractionthe reaction mixture is extracted with basic methylene chloride (2×)
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate phase is then washed with water, saline
  4. dry with materialdried over magnesiuim sulfate

Sources & evidence

ORD record
ord-a9a079948fdf475591743f7bc6d3e7ec
Source dataset
uspto-grants-2000_05
Patent number
US06057452

Reaction notes

Loading…