Hydrochloric Acid → (2S)-2-(4-chloro-benzenesulfonylamino)-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)pentanoic acid methyl ester

HRID 1987573ノート

反応式

HRID 1987573 の反応式
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]([NH2:16])[CH:5]([CH2:11][C:12]([F:15])([F:14])[F:13])[CH2:6][C:7]([F:10])([F:9])[F:8].N1C=CC=CC=1.[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][CH:26]=1.Cl>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:17])[C@@H:4]([NH:16][S:31]([C:28]1[CH:29]=[CH:30][C:25]([Cl:24])=[CH:26][CH:27]=1)(=[O:33])=[O:32])[CH:5]([CH2:6][C:7]([F:9])([F:10])[F:8])[CH2:11][C:12]([F:15])([F:14])[F:13]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73984-Chlorobenzenesulfonyl chlorideHCID 25112112(2S)-2-amino-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)-pentanoic acid methyl ester

生成物 1

HCID 25112113(2S)-2-(4-chloro-benzenesulfonylamino)-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)pentanoic acid methyl ester収率 84.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
25 °C

実験手順

To a solution of (2S)-2-amino-5,5,5-trifluoro-3-(2,2,2-trifluoroethyl)pentanoic acid methyl ester (2.173 g, 8.14 mmol) and pyridine (1.97 mL, 24.4 mmol) in CH2Cl2 (15 mL) was added a solution of 4-chlorobenzenesulfonyl chloride (2.66 g, 12.2 mmol, 97% pure) in CH2Cl2 (7 mL). The reaction mixture was stirred at 25° C. for 4 h, then cooled to 0° C. 15 mL of 1N HCl was added followed by 10 mL of dichloromethane. The phases were separated. The organic phase was washed with 1N HCl (15 mL) and brine, dried over Na2SO4, and concentrated to afford 4.1 g of crude mixture as a yellow solid. The solids were recrystallized from heptane (14 mL) to afford 3.035 g of the title product (84% yield). Mass Spectrum (+ESI): 442 [M+H]+.

後処理

  1. temperaturecooled to 0° C
  2. customThe phases were separated
  3. washThe organic phase was washed with 1N HCl (15 mL) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto afford 4.1 g of crude mixture as a yellow solid
  7. customThe solids were recrystallized from heptane (14 mL)

出典と根拠

ORDレコード
ord-a36093cf7f47453992a151119d72c4b1
出典データセット
uspto-grants-2009_06
特許番号
US07550629B2

反応ノート

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