Water → HCID 69201908、化合物

HRID 2220646ノート

反応式

HRID 2220646 の反応式
C(NC(C)C)(C)C.CS(O[CH2:13][CH2:14][O:15][C:16]1[C:21]([CH3:22])=[CH:20][C:19]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([O:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:30])=[CH:25][CH:24]=2)=[CH:18][C:17]=1[CH3:39])(=O)=O.[NH2:40][C@@H:41]([CH3:63])[C@@H:42]([C:44]1[CH:45]=[CH:46][C:47]([O:55][CH2:56][C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)=[C:48]([NH:50][S:51]([CH3:54])(=[O:53])=[O:52])[CH:49]=1)[OH:43].O>CN(C)C=O.C(OCC)(=O)C>[CH2:56]([O:55][C:47]1[CH:46]=[CH:45][C:44]([C@@H:42]([OH:43])[C@@H:41]([NH:40][CH2:13][CH2:14][O:15][C:16]2[C:17]([CH3:39])=[CH:18][C:19]([C:23]3[CH:28]=[CH:27][C:26]([C:29]([O:31][CH2:32][C:33]4[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=4)=[O:30])=[CH:25][CH:24]=3)=[CH:20][C:21]=2[CH3:22])[CH3:63])=[CH:49][C:48]=1[NH:50][S:51]([CH3:54])(=[O:53])=[O:52])[C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1

参加物

7

反応物 4

HCID 962WaterHCID 7912DiisopropylamineHCID 23090786Benzyl 4'-(2-methanesulfonyloxy-ethoxy)-3'5'-dimethylbiphenyl-4-carboxylateHCID 69202507HCID 69202507、化合物

生成物 1

HCID 69201908HCID 69201908、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

Methanesulfonyl chloride (0.102 mL) was added to a mixture of benzyl 4′-(2-hydroxyethoxy)-3′,5′-dimethylbiphenyl-4-carboxylate (0.381 g) and triethylamine (0.213 mL) in methylene chloride (5 mL) at room temperature with stirring. After being stirred at that temperature for 1 hr, water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to afford benzyl 4′-(2-methanesulfonyloxyethoxy)-3′,5′-dimethylbiphenyl-4-carboxylate as a crude product. Diisopropylamine (0.148 mL) was added to a mixture of the crude benzyl 4′-(2-methanesulfonyloxyethoxy)-3′,5′-dimethylbiphenyl-4-carboxylate and N-{5-[(1R,2S)-2-amino-1-hydoxy-propyl]-2-benzyloxyphenyl}methanesulfonamide (0.154 g) in N,N-dimethylformamide (2 mL), and the mixture was stirred at 80° C. overnight. Water and ethyl acetate were added to the reaction mixture. The organic layer was separated, washed with water and brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: methylene chloride/methanol=30/1-20/1) to afford the title compound (0.074 g).

後処理

  1. customThe organic layer was separated
  2. washwashed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent: methylene chloride/methanol=30/1-20/1)

出典と根拠

ORDレコード
ord-efab0e18371c47b2bdc3b7405f6251de
出典データセット
uspto-grants-2008_08
特許番号
US07417169B2

反応ノート

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