1-Bromo-2-Chloroethane → HCID 59062994, compound

HRID 2305648Notes

Reaction equation

HRID 2305648 reaction equation
FC1C=C(C=CC=1SC#N)N.[C:12]([NH:15][CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([S:29][C:30](C3C=CC=CC=3)(C3C=CC=CC=3)[C:31]3C=CC=CC=3)=[C:25]([F:49])[CH:24]=2)[CH2:18]1)(=[O:14])[CH3:13].BrCC[Cl:53]>CN1CCCC1=O>[C:12]([NH:15][CH2:16][C@@H:17]1[O:21][C:20](=[O:22])[N:19]([C:23]2[CH:28]=[CH:27][C:26]([S:29][CH2:30][CH2:31][Cl:53])=[C:25]([F:49])[CH:24]=2)[CH2:18]1)(=[O:14])[CH3:13]

Participants

5

Reactant 3

HCID 78491-Bromo-2-ChloroethaneHCID 222450794-Amino-2-fluorophenyl thiocyanateHCID 229661975-(S)-Acetamidomethyl-3-[4'-triphenylmethylthio-3'-fluorophenyl]oxazolidine-2-one

Product 1

HCID 59062994HCID 59062994, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Prepared according to the General Procedure for Preparation of 5-(S)-(N-Acylaminomethyl)-3-[4′-(substituted)thio-3′-fluorophenyl]oxazolidine-2-ones (Example 6) from 5-(S)-acetamidomethyl-3-[4′-(triphenylmethyl)thio-3′-fluorophenyl]-oxazolidine-2-one with 1-bromo-2-chloroethane (0.055 g, 0.38 mmol) in N-methylpyrrolidine-2-one (1 mL). The synthesis was performed at r.t. for 2 h. The crude product was purified by TLC (eluent: 10% methanol in dichloromethane). Yield 0.047 g (72%). MS (m/z): 347 [M+H]+.

Workup

  1. customPrepared
  2. customThe crude product was purified by TLC (eluent: 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-49a7bead37d349fc94840572f09fd9e2
Source dataset
uspto-grants-2002_08
Patent number
US06441005B1

Reaction notes

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