Hydrochloric Acid → (5R)-3-(4-{1-[(2S)-2,3-Dihydroxypropanoyl]-1,2,3,6-tetrahydropyridin-4-yl}-3,5-difluorophenyl)-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one

HRID 1452604Notes

Reaction equation

HRID 1452604 reaction equation
CC1(C)[O:6][C@H:5]([C:7]([N:9]2[CH2:14][CH:13]=[C:12]([C:15]3[C:20]([F:21])=[CH:19][C:18]([N:22]4[CH2:26][C@H:25]([CH2:27][N:28]5[CH:32]=[C:31]([CH3:33])[N:30]=[N:29]5)[O:24][C:23]4=[O:34])=[CH:17][C:16]=3[F:35])[CH2:11][CH2:10]2)=[O:8])[CH2:4][O:3]1.Cl.C(OCC)(=O)C>O1CCCC1>[OH:6][C@@H:5]([CH2:4][OH:3])[C:7]([N:9]1[CH2:10][CH:11]=[C:12]([C:15]2[C:20]([F:21])=[CH:19][C:18]([N:22]3[CH2:26][C@H:25]([CH2:27][N:28]4[CH:32]=[C:31]([CH3:33])[N:30]=[N:29]4)[O:24][C:23]3=[O:34])=[CH:17][C:16]=2[F:35])[CH2:13][CH2:14]1)=[O:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 57527013HCID 57527013, compound2×

Product 1

HCID 10344340(5R)-3-(4-{1-[(2S)-2,3-Dihydroxypropanoyl]-1,2,3,6-tetrahydropyridin-4-yl}-3,5-difluorophenyl)-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-oneYield 50.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(5R)-3-[4-(1-{[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]carbonyl}-1,2,3,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl]-5-[(4-methyl-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one (Intermediate 55) (542 mg, 1.08 mmol) was dissolved in tetrahydrofuran (20 ml). A solution of hydrochloric acid (1N, 10 ml) was added and the reaction mixture was stirred at room temperature. After 64 hours, the solution was poured into ethyl acetate the aqueous was extracted with ethyl acetate. The aqueous was basified with a solution of 10% aqueous sodium acetate and re-extracted with ethyl acetate. The combined organics were dried over magnesium sulfate and concentrated under vacuum. Chromatography on silica gel with 10% methanol in ethyl acetate gave 254 mg of the title product.

Workup

  1. extractionaqueous was extracted with ethyl acetate
  2. extractionre-extracted with ethyl acetate
  3. dry with materialThe combined organics were dried over magnesium sulfate
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f62889baa39d47538d91e8c6fd9c1ce9
Source dataset
uspto-grants-2009_01
Patent number
US07473699B2

Reaction notes

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