Hydrochloric Acid → (5R)-3-{3-Fluoro-4-[3-(hydroxymethyl)isoxazol-5-yl]phenyl}-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one

HRID 456787Notes

Reaction equation

HRID 456787 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][C@H:11]([CH2:13][N:14]3[CH:18]=[CH:17][N:16]=[N:15]3)[O:10][C:9]2=[O:19])[CH:5]=[CH:4][C:3]=1[C:20]1[O:24][N:23]=[C:22]([C:25](OCC)=[O:26])[CH:21]=1.[BH4-].[Li+].Cl>CO.ClCCl.CS(C)=O>[F:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][C@H:11]([CH2:13][N:14]3[CH:18]=[CH:17][N:16]=[N:15]3)[O:10][C:9]2=[O:19])[CH:5]=[CH:4][C:3]=1[C:20]1[O:24][N:23]=[C:22]([CH2:25][OH:26])[CH:21]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 10386303Ethyl 5-{2-fluoro-4-[(5R)-2-oxo-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]phenyl}isoxazole-3-carboxylate

Product 1

HCID 10066998(5R)-3-{3-Fluoro-4-[3-(hydroxymethyl)isoxazol-5-yl]phenyl}-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-oneYield 70.8%

Reagents, catalysts & solvents 1

HCID 86660116Methanol dichloromethane dimethylsulfoxideSolvent

Procedure

Ethyl 5-{2-fluoro-4-[(5R)-2-oxo-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-3-yl]phenyl}isoxazole-3-carboxylate (Example 2, 0.4 g, 1.1 mmol) was suspended in methanol/dichloromethane/dimethylsulfoxide (9 ml:3 ml:1 ml). Lithium borohydride (0.12 g, 5.5 mmol) was added portionwise. The reaction mixture was stirred under nitrogen at room temperature for 1 hour. The pH was adjusted to pH 3–4 using 1N hydrogen chloride, the mixture was cooled to 0° C., and the resulting white precipitate was collected by suction filtration. The white solid was dried in vacuo, giving 0.28 g of the desired product.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. filtrationthe resulting white precipitate was collected by suction filtration
  3. customThe white solid was dried in vacuo

Sources & evidence

ORD record
ord-5d8d5a9a2cc64a148cacbf3f86af2148
Source dataset
uspto-grants-2007_03
Patent number
US07186738B2

Reaction notes

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