Triethylamine → HCID 69980500, compound

HRID 1167438Notes

Reaction equation

HRID 1167438 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(N(CC)CC)C.[C:36]([O:39][CH2:40][C:41](Cl)=[O:42])(=[O:38])[CH3:37]>ClCCl>[C:36]([O:39][CH2:40][C:41]([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:42])(=[O:38])[CH3:37]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 26297Acetoxyacetyl chlorideHCID 69980303HCID 69980303, compound

Product 1

HCID 69980500HCID 69980500, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-(piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one dihydrochloride (1.29 g, 3 mmol) was suspended in dichloromethane (25 ml) under nitrogen at ambient temperature. Triethylamine (1.06 g, 10.5 mmol) was added, to give a solution after 15 minutes. The mixture was cooled to 4°, and acetoxyacetyl chloride (410 mg, 3 mmol) was added dropwise. The mixture was stirred for 18 hours at ambient temperature, washed with water (2×20 ml), saturated brine (20 ml), and dried (magnesium sulfate). The residue was purified by chromatography on a 20 g silica Mega Bond Elut® column, eluting with a gradient increasing in polarity from 0 to 5% MeOH in dichloromethane. Relevant fractions were combined and evaporated to give the desired product (1.16 g).

Workup

  1. customto give a solution after 15 minutes
  2. temperatureThe mixture was cooled to 4°
  3. washwashed with water (2×20 ml), saturated brine (20 ml)
  4. dry with materialdried (magnesium sulfate)
  5. customThe residue was purified by chromatography on a 20 g silica Mega Bond Elut® column
  6. washeluting with a gradient
  7. temperatureincreasing in polarity from 0 to 5% MeOH in dichloromethane
  8. customevaporated

Sources & evidence

ORD record
ord-f1be39b0682a434d989554046ff939c4
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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