Pyridine → Isohexane ethyl acetate

HRID 8145Notes

Reaction equation

HRID 8145 reaction equation
O1C=CC(N(C[C@@H]2OC(=O)N(C3C=CC(N4[CH2:33][CH2:32][CH:31]=[CH:30][CH2:29]4)=C(F)C=3)C2)[C:7]([O:9][CH2:10][C:11](Cl)(Cl)Cl)=[O:8])=N1.N1C=CC=C[CH:36]=1>ClCCl>[C:7]([O:9][CH2:10][CH3:11])(=[O:8])[CH3:36].[CH3:33][CH2:32][CH2:31][CH:30]([CH3:29])[CH3:36]

Participants

4

Reactant 2

HCID 1049PyridineHCID 867601825(R)-[N-isoxazol-3-yl-N-(2,2,2-trichloroethyloxycarbonyl)-aminomethyl]-3-[3-fluoro-4-(1,2,5,6-tetrahydropyrid yl)phenyl]oxazolidin-2-one

Product 1

HCID 21882781Isohexane ethyl acetateYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 5(R)-[N-isoxazol-3-yl-N-(2,2,2-trichloroethyloxycarbonyl)-aminomethyl]-3-[3-fluoro-4-(1,2,5,6-tetrahydropyrid yl)phenyl]oxazolidin-2-one (228 mg, 0.4 mM) in dry dichloromethane (5 ml) at 0–4° C., was added pyridine (158 mg, 2.0 mM) followed by dropwise addition of a solution of (S)-(+)-2,3,0-isopropylideneglycinoyl chloride (EP 0 413 401 A2; 200 mg, 1.2 mM) in dichloromethane (1 ml). The solution was stirred at 0–4° C. for 10 min. and then allowed to warm to ambient temperature. The reaction mixture was washed with water and brine, dried over sodium sulfate and evaporated to a gum. The title compound was isolated by MPLC (60% ethyl acetate/isohexane) and was obtained as a crisp foam on evaporation (158 mg, 60%).

Workup

  1. washThe reaction mixture was washed with water and brine
  2. dry with materialdried over sodium sulfate
  3. customevaporated to a gum

Sources & evidence

ORD record
ord-a773cec767284af9a5ce45a2ddd1fe40
Source dataset
uspto-grants-2006_08
Patent number
US07087629B2

Reaction notes

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