Tetrahydrofuran → N-[[(5S)-3-[3-Fluoro-4-[tetrahydro-1,1-dioxido-2-(2-propenyl)-2H-1,2-thiazin-4-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

HRID 1699658Notes

Reaction equation

HRID 1699658 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:19][C:20](=[O:29])OCC2C=CC=CC=2)[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[N:10]([CH2:16][CH:17]=[CH2:18])[CH2:9]1.C([Li])CCC.O1[CH2:37][C@@H:36]1[CH2:38][NH:39][C:40](=[O:42])[CH3:41].C1C[O:46]CC1>CCCCCC>[F:1][C:2]1[CH:3]=[C:4]([N:19]2[CH2:37][C@H:36]([CH2:38][NH:39][C:40](=[O:42])[CH3:41])[O:29][C:20]2=[O:46])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[N:10]([CH2:16][CH:17]=[CH2:18])[CH2:9]1

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 11051615Acetamide, N-[(2S)-oxiranylmethyl]-HCID 12019397Phenylmethyl [3-fluoro-4-[tetrahydro-1,1-dioxido-2-(2-propenyl)-2H-1,2-thiazin-4-yl]phenyl]carbamateHCID 178418339Butyllithium

Product 1

HCID 9910287N-[[(5S)-3-[3-Fluoro-4-[tetrahydro-1,1-dioxido-2-(2-propenyl)-2H-1,2-thiazin-4-yl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamideYield 73%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

Phenylmethyl [3-fluoro-4-[tetrahydro-1,1-dioxido-2-(2-propenyl)-2H-1,2-thiazin-4-yl]phenyl]carbamate (1.70 g, 4.07 mmol) is dissolved in dry THF (18 ml) under nitrogen and cooled to −78°. A 1.6 M solution of n-butyl lithium (2.7 ml, 4.32 mmol) in hexane is added and stirred for 1 hr. A solution of N-[(2S)oxiranylmethyl]acetamide 11 (960 mg, 8.35 mmol) in dry THF (6.5 ml) is added and the stirred mixture allowed to come to 25° overnight. Solvent is evaporated and the residue partitioned between chloroform (100 ml) and ammonium chloride solution (50 ml). The organic layer is washed with brine (40 ml), dried (MgSO4) and evaporated. The residue is chromatographed over silica gel (150 g) eluting with 24% methanol-chloroform to afford the oxazolidinone as a white foam (1.275 g, 73%). HRMS(FAB) calcd for m+H=426.1499; Found: 426.1506.

Workup

  1. temperaturecooled to −78°
  2. waitto come to 25° overnight
  3. customSolvent is evaporated
  4. customthe residue partitioned between chloroform (100 ml) and ammonium chloride solution (50 ml)
  5. washThe organic layer is washed with brine (40 ml)
  6. dry with materialdried (MgSO4)
  7. customevaporated
  8. customThe residue is chromatographed over silica gel (150 g)
  9. washeluting with 24% methanol-chloroform

Sources & evidence

ORD record
ord-c5be3eaa312845d0871cd9ad980230af
Source dataset
uspto-grants-2002_02
Patent number
US06348459B1

Reaction notes

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