Diisopropylethylamine → HCID 59223849、化合物

HRID 1158450ノート

反応式

HRID 1158450 の反応式
[CH:1]([C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][C:4]=1[OH:12])=[O:2].[CH3:13][O:14][CH2:15][CH2:16][CH2:17]OS(C1C=CC(C)=CC=1)=O.[CH:28](N(C(C)C)CC)([CH3:30])[CH3:29].N[C@H]([C:50](O)=[O:51])CC1C=C2C(C=CC=C2)=CC=1>CN(C=O)C>[CH3:50][O:51][CH2:29][CH2:28][CH2:30][O:8][C:7](=[O:9])[C:6]1[CH:10]=[CH:11][C:3]([CH:1]=[O:2])=[C:4]([O:12][CH2:17][CH2:16][CH2:15][O:14][CH3:13])[CH:5]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 1859152-NaphthylalanineHCID 3175084-Formyl-3-hydroxybenzoic acidHCID 68617130HCID 68617130、化合物

生成物 1

HCID 59223849HCID 59223849、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

A mixture of 4-formyl-3-hydroxybenzoic acid (1.5 g, 8.8 mmol), 4-methyl-benzenesulfinic acid 3-methoxy-propyl ester (4.5 g, 18.4 mmol), diisopropylethylamine (3.4 mL, 19.3 mmol) and Nal (2.63 g, 17.5 mmol) in DMF (20 mL) is stirred at 80° C. for 60 h and at 130° C. for another 5 h. The solvent is partially removed under reduced pressure, water is added and the mixture is extracted with ethyl acetate. Washing (brine) and drying (Na2SO4) of the combined organic extracts, filtration and evaporation of the solvent affords the crude product. The desired product is obtained by flash chromatography on silica gel (eluent: c-hexane/AcOEt 3:1). MS (LC-MS): 311.1 [M+H]+; tR (Zorbax SB C18 column, 10-95% CH3CN/H2O/0.8 min, 95% CH3CN/H2O, 0.7 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 mL/min): 1.20 min.

後処理

  1. customThe solvent is partially removed under reduced pressure, water
  2. additionis added
  3. extractionthe mixture is extracted with ethyl acetate
  4. washWashing (brine)
  5. customdrying
  6. filtration(Na2SO4) of the combined organic extracts, filtration and evaporation of the solvent
  7. customaffords the crude product

出典と根拠

ORDレコード
ord-0f101a88715348b3beda1245743c82f9
出典データセット
uspto-grants-2010_10
特許番号
US07807709B2

反応ノート

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