Methyl chloroformate → HCID 497407, compound

HRID 1167441Notes

Reaction equation

HRID 1167441 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.Cl[C:37]([O:39][CH3:40])=[O:38]>ClCCl>[CH3:40][O:39][C:37]([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:38]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 69980303HCID 69980303, compound

Product 1

HCID 497407HCID 497407, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(4-(piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one dihydrochloride (866 mg, 2 mmol) was suspended in dichloromethane (40 ml) under nitrogen at ambient temperature. Triethylamine (707 mg, 7 mmol) was added, followed by methyl chloroforrnate (190 mg, 2 mmol). The mixture was stirred for 2 hours at ambient temperature, washed with water (2×50 ml), saturated brine (50 ml), and dried (magnesium sulfate). After filtration and evaporation, the residue was triturated with diethyl ether to give the desired product (689 mg).

Workup

  1. washwashed with water (2×50 ml), saturated brine (50 ml)
  2. dry with materialdried (magnesium sulfate)
  3. filtrationAfter filtration and evaporation
  4. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-b512e7b0f34e4f8b999a933272f3f270
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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