Chloroacetyl chloride → HCID 69981735, compound

HRID 1167447Notes

Reaction equation

HRID 1167447 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].Cl.Cl.[N:8]1([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][O:26][C:27]4[CH:31]=[CH:30][O:29][N:28]=4)[O:22][C:21]3=[O:32])=[CH:16][C:15]=2[F:33])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1.C(N(CC)CC)C>ClCCl>[Cl:1][CH2:2][C:3]([N:11]1[CH2:10][CH2:9][N:8]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][O:26][C:27]4[CH:31]=[CH:30][O:29][N:28]=4)[O:22][C:21]3=[O:32])=[CH:16][C:15]=2[F:33])[CH2:13][CH2:12]1)=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 69980303HCID 69980303, compound

Product 1

HCID 69981735HCID 69981735, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Chloroacetyl chloride (114 mg, 1 mmol) was added to a stirred solution of 3-(4-(piperazin-1-yl)-3-fluorophenyl)-5(R)-(isoxazol-3-yloxymethyl)oxazolidin-2-one dihydrochloride (435 mg, 1 mmol) and triethylamine (302 mg, 3 mmol) in dichloromethane (10 ml) at ambient temperature. After 10 minutes the reaction was purified by direct chromatography on a 10 g silica Mega Bond Elut® column, eluting with dichloromethane. Relevant fractions were combined and evaporated to give the desired product (390 mg). MS (ESP): 439 (MH+) for C19H20ClFN4O5;

Workup

  1. customAfter 10 minutes the reaction was purified by direct chromatography on a 10 g silica Mega Bond Elut® column
  2. washeluting with dichloromethane
  3. customevaporated

Sources & evidence

ORD record
ord-6cdbd68ab9de42e2ba72e3ae78b595fd
Source dataset
uspto-grants-2003_09
Patent number
US06617339B1

Reaction notes

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