1-((1S)-1-isocyanatoethyl)naphthalene → (1-Naphthalen-1-yl-ethyl)-carbamic acid-4-benzo [1,3]dioxol-5-yl-2-(4-methoxy-phenyl)-5-oxo-3-(3,4,5-trimethoxy-benzyl)-2,5-dihydro-furan-2-yl ester

HRID 582090ノート

反応式

HRID 582090 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11](=[O:37])[O:12][C:13]([OH:36])([C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[C:14]=3[CH2:15][C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.[C:38]1([C@@H:48]([N:50]=[C:51]=[O:52])[CH3:49])[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[CH:41]=[CH:40][CH:39]=1>CN(C)C1C=CN=CC=1.ClCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11](=[O:37])[O:12][C:13]([O:36][C:51](=[O:52])[NH:50][CH:48]([C:38]4[C:47]5[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=5)[CH:41]=[CH:40][CH:39]=4)[CH3:49])([C:28]4[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=4)[C:14]=3[CH2:15][C:16]3[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

参加物

5

反応物 2

HCID 70235101-((1S)-1-isocyanatoethyl)naphthaleneHCID 9870830CI 1020

生成物 1

HCID 15411000(1-Naphthalen-1-yl-ethyl)-carbamic acid-4-benzo [1,3]dioxol-5-yl-2-(4-methoxy-phenyl)-5-oxo-3-(3,4,5-trimethoxy-benzyl)-2,5-dihydro-furan-2-yl ester

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To 15 mL dichloromethane was added 3-benzo[1,3]dioxol-5-yl-5-hydroxy-5-(4-methoxyphenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one 1.00 g (1.98 mmol) and stirred to dissolve. To this was added (S)-1-(1-naphthyl)ethyl isocyanate 414 mg (2.1 mmol) and a catalytic amount of 4-dimethylaminopyridine 20 mg (0.164 mmol). The mixture was stirred at room temperature for 24 hours. The solution was washed with 50 mL water and 50 mL brine, and the organic phase was separated and dried over magnesium sulfate, then evaporated to dryness. The crude product was then purified by flash chromatography (150 g silica gel, 10% EtOAc/CH2Cl2). The product was isolated by evaporation of the appropriate fractions to give 840 mg (60%) as a white foam. The product was identified by 1H NMR, MS, [M+H]+ =704 Da. and microanalysis.

後処理

  1. dissolutionto dissolve
  2. stirringThe mixture was stirred at room temperature for 24 hours
  3. washThe solution was washed with 50 mL water and 50 mL brine
  4. customthe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated to dryness
  7. customThe crude product was then purified by flash chromatography (150 g silica gel, 10% EtOAc/CH2Cl2)
  8. customThe product was isolated by evaporation of the appropriate fractions
  9. customto give 840 mg (60%) as a white foam

出典と根拠

ORDレコード
ord-32c35bab1d40449c8ec5981052b0d01d
出典データセット
uspto-grants-1999_07
特許番号
US05922759

反応ノート

読み込み中…