4-Methylmorpholine → 2-Cyclohexylmethyl-1-(4-isopropyl-2-oxooxazolidin-3-yl)-4-morpholin-4-ylbutane-1,4-dione

HRID 1060745노트

반응식

HRID 1060745 반응식
[CH:1]1([CH2:7][CH:8]([C:13]([N:15]2[CH:19]([CH:20]([CH3:22])[CH3:21])[CH2:18][O:17][C:16]2=[O:23])=[O:14])[CH2:9][C:10]([OH:12])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:48]1[CH2:53][CH2:52][O:51][CH2:50][CH2:49]1.CN1CCOCC1>CN(C=O)C>[CH:1]1([CH2:7][CH:8]([CH2:9][C:10]([N:48]2[CH2:53][CH2:52][O:51][CH2:50][CH2:49]2)=[O:12])[C:13]([N:15]2[CH:19]([CH:20]([CH3:22])[CH3:21])[CH2:18][O:17][C:16]2=[O:23])=[O:14])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 8083MorpholineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 186287363-Cyclohexylmethyl-4-(4-isopropyl-2-oxooxazolidin-3-yl)-4-oxobutyric acid

생성물 1

HCID 186286692-Cyclohexylmethyl-1-(4-isopropyl-2-oxooxazolidin-3-yl)-4-morpholin-4-ylbutane-1,4-dione수율 67.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3-cyclohexylmethyl-4-(4-isopropyl-2-oxooxazolidin-3-yl)-4-oxobutyric acid (2.00 g, 6.14 mmol) and HBTU (2.56 g, 6.76 mmol) in DMF (20 mL) were treated with morpholine (0.591 mL, 6.76 mmol) and N-methylmorpholine (0.811 mL, 7.37 mmol). The mixture was stirred overnight at ambient temperature and then partitioned between 4:1:2:3 ethyl acetate/THF/water/brine (100 mL total). The organic phase was washed with 1M hydrochloric acid, saturated aqueous sodium bicarbonate and brine (50 mL each), dried (MgSO4) filtered and concentrated to dryness. The residue dissolved in ethyl acetate/hexane and product was crystallized out to provide 2-cyclohexylmethyl-1-(4-isopropyl-2-oxooxazolidin-3-yl)-4-morpholin-4-ylbutane-1,4-dione (1.63 g). MS (M+1): 395.

후처리

  1. custompartitioned between 4:1:2:3 ethyl acetate/THF/water/brine (100 mL total)
  2. washThe organic phase was washed with 1M hydrochloric acid, saturated aqueous sodium bicarbonate and brine (50 mL each)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. dissolutionThe residue dissolved in ethyl acetate/hexane
  7. customproduct was crystallized out

출처 및 근거

ORD 기록
ord-77e78dabc7ac454d849ab74c4060a049
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525036B2

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