Triethylamine → Methyl 3-[(2-tert-butoxy-2-oxo-1-phenylethyl)sulfamoyl]benzoate

HRID 1529530ノート

反応式

HRID 1529530 の反応式
[C:1]([O:5][C:6](=[O:15])[CH:7]([NH2:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Cl[S:17]([C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([O:25][CH3:26])=[O:24])(=[O:19])=[O:18].C(N(CC)CC)C>O1CCCC1>[C:1]([O:5][C:6](=[O:15])[CH:7]([NH:14][S:17]([C:20]1[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=1)[C:23]([O:25][CH3:26])=[O:24])(=[O:19])=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 113339Benzoic acid, 3-(chlorosulfonyl)-, methyl esterHCID 12162441HCID 12162441、化合物

生成物 1

HCID 86720693Methyl 3-[(2-tert-butoxy-2-oxo-1-phenylethyl)sulfamoyl]benzoate収率 43.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred solution of tert-butyl-2-amino-2-phenylacetate (1.34 g, 6.45 mmol) and methyl 3-(chlorosulfonyl)benzoate (1.53 g, 6.51 mmol) in tetrahydrofuran (15 mL) was added triethylamine (0.90 mL, 6.45 mmol) in one portion at ambient temperature. The reaction mixture was stirred for 30 minutes, after which time, the reaction mixture was concentrated under reduced pressure and partitioned between ethyl acetate (30 mL) and 10% citric acid solution (10 mL). The resulting organic phases were dried over magnesium sulfate and concentrated under reduced pressure to yield a crude solid. The solid was triturated in diethyl ether (5 mL) and cold methanol (5 mL) to yield the title compound as a white solid (1.13 g, 43%).

後処理

  1. concentrationafter which time, the reaction mixture was concentrated under reduced pressure
  2. custompartitioned between ethyl acetate (30 mL) and 10% citric acid solution (10 mL)
  3. dry with materialThe resulting organic phases were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto yield a crude solid
  6. customThe solid was triturated in diethyl ether (5 mL)

出典と根拠

ORDレコード
ord-7d85209e3f1244728aa3851869eca2c7
出典データセット
uspto-grants-2015_07
特許番号
US09090606B2

反応ノート

読み込み中…