Acetyl chloride → 3-(4-(4-Acetylpiperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxy-methyl)oxazolidin-2-one

HRID 1167439Notes

Reaction equation

HRID 1167439 reaction equation
Cl.Cl.[N:3]1([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20][O:21][C:22]4[CH:26]=[CH:25][O:24][N:23]=4)[O:17][C:16]3=[O:27])=[CH:11][C:10]=2[F:28])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.[C:29](Cl)(=[O:31])[CH3:30]>>[C:29]([N:6]1[CH2:5][CH2:4][N:3]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:19][C@H:18]([CH2:20][O:21][C:22]4[CH:26]=[CH:25][O:24][N:23]=4)[O:17][C:16]3=[O:27])=[CH:11][C:10]=2[F:28])[CH2:8][CH2:7]1)(=[O:31])[CH3:30]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 69980303HCID 69980303, compound

Product 1

HCID 699817043-(4-(4-Acetylpiperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxy-methyl)oxazolidin-2-one

Procedure

The title compound was prepared using essentially the method of Example 73, starting from 3-(4-(piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one dihydrochloride (0.59 g, 1.35 mmol) and acetyl chloride. Purification by chromatography, eluting with a gradient increasing in polarity from 0 to 2.5% MeOH in dichloromethane gave the desired product (142 mg).

Workup

  1. customThe title compound was prepared
  2. customPurification by chromatography
  3. washeluting with a gradient
  4. temperatureincreasing in polarity from 0 to 2.5% MeOH in dichloromethane

Sources & evidence

ORD record
ord-4ee6c779d78f419699eb71668cb47347
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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