Chloroacetyl chloride → HCID 69365788, compound

HRID 723754Notes

Reaction equation

HRID 723754 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][N:21]4[CH:25]=[CH:24][N:23]=[N:22]4)[O:17][C:16]3=[O:26])=[CH:11][C:10]=2[F:27])[CH2:8][CH2:7][NH:6][CH2:5][CH2:4]1.C(N(CC)CC)C.[Cl:35][CH2:36][C:37](Cl)=[O:38]>ClCCl>[Cl:35][CH2:36][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][N:21]4[CH:25]=[CH:24][N:23]=[N:22]4)[O:17][C:16]3=[O:26])=[CH:11][C:10]=2[F:27])[CH2:8][CH2:7]1)=[O:38]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 69364107HCID 69364107, compound

Product 1

HCID 69365788HCID 69365788, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(5R)-3-(4-(piperazin-1-yl)-3-fluorophenyl)-5-(1,2,3-triazol-1-ylmethyl)oxazolidin-2-one dihydrochloride (4.19 g, 10 mM) was suspended in dry dichloromethane (100 ml) under nitrogen and treated with triethylamine (3.03 g, 30 mM) to give a solution. After cooling to 4°, chloroacetyl chloride (1.14 g, 10 mM) was added and the mixture stirred for 15 minutes. The volume was reduced to 20 ml, and the solution chromatographed on silica, eluting with dichloromethane (30 ml). Relevant fractions were combined, washed with water (50 ml) and dried (magnesium sulfate). Evaporation gave the desired product (2.86 g).

Workup

  1. customto give a solution
  2. temperatureAfter cooling to 4°
  3. customthe solution chromatographed on silica
  4. washeluting with dichloromethane (30 ml)
  5. washwashed with water (50 ml)
  6. dry with materialdried (magnesium sulfate)
  7. customEvaporation

Sources & evidence

ORD record
ord-fb2c986980f64bc28a7d2df9d3e1218e
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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