Sulfuric Acid → HCID 57551904、化合物

HRID 1258488ノート

反応式

HRID 1258488 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:13][C@@H:14]([CH2:18][CH:19]([CH3:21])[CH3:20])[C:15]([OH:17])=[O:16])[C:9]([F:12])([F:11])[F:10])=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[CH:27](O)([CH3:29])[CH3:28]>>[CH:27]([O:16][C:15](=[O:17])[C@@H:14]([NH:13][C@@H:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[C:9]([F:12])([F:11])[F:10])[CH2:18][CH:19]([CH3:21])[CH3:20])([CH3:29])[CH3:28]

参加物

4

反応物 3

HCID 1118Sulfuric AcidHCID 3776IsopropanolHCID 57446946N-[(1S)-1-(4-Bromophenyl)-2,2,2-trifluoroethyl]-L-leucine

生成物 1

HCID 57551904HCID 57551904、化合物収率 88%

反応条件

温度
80 °C

実験手順

To a stirred solution of (S)-2-[(S)-1-(4-bromo-phenyl)-2,2,2-trifluoro-ethylamino]-4-methyl-pentanoic acid, prepared as shown in Li, C. S. et al Bioorg. Med. Chem. Lett. 2006, 16, 1985, (1.80 g, 4.9 mmol) in isopropyl alcohol (100 mL) was added concentrated sulphuric acid (2 mL). The resulting solution was heated at 80° C. for 4 hours. The reaction mixture was allowed to cool and was then concentrated in vacuo. The resulting oil was dispersed in CH2Cl2 (100 mL), washed with saturated NaHCO3 (2×50 mL), dried (MgSO4) and concentrated in vacuo to yield the title compound as a brown oil (1.77 g, 88%). MS [M+H] 412.

後処理

  1. temperatureto cool
  2. concentrationwas then concentrated in vacuo
  3. additionThe resulting oil was dispersed in CH2Cl2 (100 mL)
  4. washwashed with saturated NaHCO3 (2×50 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f8d6b283398d4a3ea2a37d5b8a1e7640
出典データセット
uspto-grants-2013_06
特許番号
US08466158B2

反応ノート

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