1-Chloroethyl chloroformate → HCID 69363543, compound

HRID 723795Notes

Reaction equation

HRID 723795 reaction equation
ClC(OC(Cl)C)=O.C([N:15]1[CH2:20][CH2:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:31][C@H:30]([CH2:32][N:33]4[N:37]=[N:36][CH:35]=[N:34]4)[O:29][C:28]3=[O:38])=[CH:23][C:22]=2[F:39])=[CH:17][CH2:16]1)C1C=CC=CC=1>ClCCl.C(N(CC)C(C)C)(C)C>[NH:15]1[CH2:20][CH2:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([N:27]3[CH2:31][C@H:30]([CH2:32][N:33]4[N:37]=[N:36][CH:35]=[N:34]4)[O:29][C:28]3=[O:38])=[CH:23][C:22]=2[F:39])=[CH:17][CH2:16]1

Participants

5

Reactant 2

HCID 5213051-Chloroethyl chloroformateHCID 69364497HCID 69364497, compound

Product 1

HCID 69363543HCID 69363543, compoundYield 86.7%

Reagents, catalysts & solvents 2

HCID 81531DiisopropylethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

1-Chloroethyl chloroformate (1.18 g, 8.3 mM) was added dropwise, under an atmosphere of nitrogen, to a stirred solution of (5R)-3-(4-(1-benzyl-1,2,5,6-tetrahydropyridin-4-yl)-3-fluoro-phenyl)-5-(tetrazol-2-ylmethyl)oxazolidin-2-one (2.56 g, 5.90 mM) and N,N-diisopropylethylamine (0.230 mg, 1.77 mM) in dichloromethane (50 ml) with cooling in ice/water. The reaction was stirred for 30 minutes at ice temperature, and the brown solution purified by MPLC on silica, eluting with 75% ethyl acetate in isohexane. The resulting carbamate intermediate was dissolved in methanol (60 ml) and heated at 60° for 30 minutes. Evaporation of the solvent and trituration with diethyl ether gave the title compound (1.76 g) as its hydrochloride salt. MS (ESP): 345 (MH+) for C16H17FN6O2

Workup

  1. customthe brown solution purified by MPLC on silica
  2. washeluting with 75% ethyl acetate in isohexane
  3. dissolutionThe resulting carbamate intermediate was dissolved in methanol (60 ml)
  4. temperatureheated at 60° for 30 minutes
  5. customEvaporation of the solvent and trituration with diethyl ether

Sources & evidence

ORD record
ord-7a33acd654d04ddbb063a5d030dfee22
Source dataset
uspto-grants-2006_11
Patent number
US07141583B2

Reaction notes

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