Hydrochloric Acid → HCID 9824949, compound

HRID 723792Notes

Reaction equation

HRID 723792 reaction equation
CC1(C)[O:6][C@H:5]([C:7]([N:9]2[CH2:14][CH2:13][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]=[CH:31][N:30]=[N:29]5)[O:24][C:23]4=[O:33])=[CH:17][C:16]=3[F:34])=[CH:11][CH2:10]2)=[O:8])[CH2:4][O:3]1.Cl>O1CCCC1>[OH:6][C@@H:5]([CH2:4][OH:3])[C:7]([N:9]1[CH2:14][CH2:13][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]=[CH:31][N:30]=[N:29]4)[O:24][C:23]3=[O:33])=[CH:17][C:16]=2[F:34])=[CH:11][CH2:10]1)=[O:8]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69364522(5R)-3-(4-(1-((4S)-2,2-dimethyl-1,3-dioxolane-4-carbonyl)-1,2,5,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one

Product 1

HCID 9824949HCID 9824949, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (5R)-3-(4-(1-((4S)-2,2-dimethyl-1,3-dioxolane-4-carbonyl)-1,2,5,6-tetrahydropyridin-4-yl)-3,5-difluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one (700 mg, 1.43 mM) in tetrahydrofuran (25 ml) was added aqueous hydrochloric acid (1M, 15 ml) and the mixture stirred at ambient temperature for 2 days. Solvent was evaporated and the residue treated with water (10 ml). Aqueous sodium acetate (10%, 10 ml) was added, and the precipitate filtered and washed with ethanol and diethyl ether to give the title compound (514 mg).

Workup

  1. customSolvent was evaporated
  2. additionthe residue treated with water (10 ml)
  3. additionAqueous sodium acetate (10%, 10 ml) was added
  4. filtrationthe precipitate filtered
  5. washwashed with ethanol and diethyl ether

Sources & evidence

ORD record
ord-acdc0c17482241de8eca74389b217ad2
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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