Triphenylphosphine → HCID 67330598, 화합물

HRID 1942448노트

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HRID 1942448 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[C:15]([O:20][CH2:21][CH3:22])(=[O:19])[C@H:16]([CH3:18])O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1.O>[CH2:21]([O:20][C:15](=[O:19])[C@@H:16]([CH3:18])[O:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13])[CH3:22]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl esterHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 92831(L)-ethyl lactate

생성물 1

HCID 67330598HCID 67330598, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of methyl 4-hydroxy-3-nitrobenzoate (5.0 g) and ethyl L-lactate (2.9 ml) in tetrahydrofuran (120 ml) was added triphenylphosphine (10 g), and the mixture was stirred at room temperature for 10 minutes. To the mixture was added under ice-cooling diisopropyl azodicarboxylate (20 ml), and the mixture was stirred at 60° C. for 4 hours. The reaction solution was cooled to room temperature, and water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, filtered and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give the title compound (9.5 g).

후처리

  1. additionTo the mixture was added under ice-
  2. stirringthe mixture was stirred at 60° C. for 4 hours
  3. temperatureThe reaction solution was cooled to room temperature
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)

출처 및 근거

ORD 기록
ord-5e50d3d924e248c0956dc57732889bc5
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389511B2

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