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

HRID 1060745ノート

反応式

HRID 1060745 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-77e78dabc7ac454d849ab74c4060a049
出典データセット
uspto-grants-2003_02
特許番号
US06525036B2

反応ノート

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