4-Methylmorpholine → Benzyl 4-(4-fluorophenyl)-2,5-dioxooxazolidine-3-carboxylate

HRID 625747Notes

Reaction equation

HRID 625747 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:12](=[O:13])[O:11][C:10](=[O:14])[NH:9]2)=[CH:4][CH:3]=1.Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].CN1CCOCC1>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]2[C:12](=[O:13])[O:11][C:10](=[O:14])[N:9]2[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:17])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 79724-MethylmorpholineHCID 10387Benzyl chloroformateHCID 866490494-(4-Fluorophenyl)oxazolidine-2,5-dione

Product 1

HCID 11438888Benzyl 4-(4-fluorophenyl)-2,5-dioxooxazolidine-3-carboxylateYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(4-fluorophenyl)oxazolidine-2,5-dione (2.5 g, 12.8 mmol) in THF (30 mL) cooled to −25° C. was added benzyl chloroformate (2.3 mL, 16.6 mmol), followed by the slow addition (˜10 min) of N-methylmorpholine (2.11 mL, 19.2 mmol) as a solution in THF (5 mL). The solution was stirred at this temperature for 1 h. and then allowed to warm to rt overnight. The resulting solution was filtered through Celite, and the filtrate was concentrated. The resulting crude material was recrystallized from 2:2:1 t-butyl methyl ether:hexanes:THF to give benzyl 4-(4-fluorophenyl)-2,5-dioxooxazolidine-3-carboxylate (2.7 g, 64%) which was used without further purification.

Workup

  1. filtrationThe resulting solution was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe resulting crude material was recrystallized from 2:2:1 t-butyl methyl ether

Sources & evidence

ORD record
ord-0d89d39743bb41238d6a0d06399a9d11
Source dataset
uspto-grants-2016_04
Patent number
US09308207B2

Reaction notes

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