HCID 86723051, compound → HCID 86723050, compound

HRID 1405612Notes

Reaction equation

HRID 1405612 reaction equation
[C:1](O[K])(C)(C)C.[O:7]=[C:8]1[N:12]([C:13]2[CH:14]=[CH:15][C:16]3[O:21][CH2:20][C:19](=[O:22])[NH:18][C:17]=3[CH:23]=2)[CH2:11][C@H:10]([CH2:24][CH2:25][CH:26]=O)[O:9]1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.O>[CH2:24]([CH:10]1[O:9][C:8](=[O:7])[N:12]([C:13]2[CH:14]=[CH:15][C:16]3[O:21][CH2:20][C:19](=[O:22])[NH:18][C:17]=3[CH:23]=2)[CH2:11]1)[CH2:25][CH:26]=[CH2:1]

Participants

6

Reactant 2

HCID 86723051HCID 86723051, compoundHCID 178418922HCID 178418922, compound

Product 1

HCID 86723050HCID 86723050, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of methyltriphenylphosphonium bromide (2.03 g) in THF (6 ml) was treated with tBuOK (638 mg) and the reaction mixture was further stirred at rt for 1 h. The mixture was cooled to 0° C. and treated with a suspension of 3-[(S)-2-oxo-3-(3-oxo-3,4-dihydro-2H-benzo[1,4]oxazin-6-yl)-oxazolidin-5-yl]-propionaldehyde (1.50 g; prepared according to WO 2010/041194, example AV) in THF (11 ml). The reaction mixture was stirred at 0° C. for 30 min and allowed to reach rt. The reaction mixture was diluted with water and the org. layer was separated. The aq. layer was extracted with EA. The combined org. extracts were washed with brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by CC (Hex/EA 4:1), affording a yellow solid (1.25 g; 84% yield).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. stirringThe reaction mixture was stirred at 0° C. for 30 min
  3. customto reach rt
  4. customlayer was separated
  5. extractionThe aq. layer was extracted with EA
  6. washextracts were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by CC (Hex/EA 4:1)
  11. customaffording a yellow solid (1.25 g; 84% yield)

Sources & evidence

ORD record
ord-8be39b4500d345cab9c601dbe209ac46
Source dataset
uspto-grants-2014_12
Patent number
US08916573B2

Reaction notes

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