Triethylamine → methyl 4-[(1S)-1-[[(2R)-3-methyl-2-methylsulfonyloxy-butanoyl]amino]ethyl]benzoate

HRID 1466537ノート

反応式

HRID 1466537 の反応式
[OH:1][C@H:2]([CH:18]([CH3:20])[CH3:19])[C:3]([NH:5][C@H:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)[CH3:7])=[O:4].C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[CH3:19][CH:18]([CH3:20])[C@@H:2]([O:1][S:29]([CH3:28])(=[O:31])=[O:30])[C:3]([NH:5][C@H:6]([C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=1)[CH3:7])=[O:4]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86730613methyl 4-[(1S)-1-[[(2R)-2-hydroxy-3-methyl-butanoyl]amino]ethyl]benzoate

生成物 1

HCID 86730615methyl 4-[(1S)-1-[[(2R)-3-methyl-2-methylsulfonyloxy-butanoyl]amino]ethyl]benzoate収率 98%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A mixture of methyl 4-[(1S)-1-[[(2R)-2-hydroxy-3-methyl-butanoyl]amino]ethyl]benzoate (40 g; 143 mmol), and triethylamine (22.0 mL, 157 mmol) in CH2Cl2 (400 mL) is cooled to 0° C. A solution of methanesulfonyl chloride (11.1 mL, 143 mmol) in CH2Cl2 (200 mL) is added dropwise over 45 min, and the mixture is stirred to room temperature for 1 h. The mixture is washed sequentially with 1N HCl (100 mL) and aq. NaHCO3 (200 mL). The organic layer is dried over MgSO4, filtered, and concentrated. The crude material is slurried in methyl t-butyl ether (200 mL) and hexane (600 mL) for 30 min, filtered, and dried under vacuum to provide the title compound as a white solid (50 g, 98%). MS (m/z): 358.2 (M+1).

後処理

  1. washThe mixture is washed sequentially with 1N HCl (100 mL) and aq. NaHCO3 (200 mL)
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. waithexane (600 mL) for 30 min
  6. filtrationfiltered
  7. customdried under vacuum

出典と根拠

ORDレコード
ord-95f69a7476334911ad78c16dcc449f1b
出典データセット
uspto-grants-2015_04
特許番号
US09000043B2

反応ノート

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