Lithium Hydroxide → (4S)-2-(4-carboxy-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine

HRID 276299ノート

反応式

HRID 276299 の反応式
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]2[N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C@@H:15]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:14][S:13]2)=[C:7]([CH3:25])[CH:6]=1)=[O:4].[Li+].[OH-]>CO.O>[C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]=[C:12]2[N:16]([CH2:17][CH:18]([CH3:20])[CH3:19])[C@@H:15]([CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:14][S:13]2)=[C:7]([CH3:25])[CH:6]=1)([OH:4])=[O:2]

参加物

5

反応物 2

HCID 3939Lithium HydroxideHCID 56989530(4S)-2-(4-methoxycarbonyl-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine

生成物 1

HCID 57222223(4S)-2-(4-carboxy-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine収率 100%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of (4S)-2-(4-methoxycarbonyl-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine (prepared in a manner analogous to that described in Method D2a; 0.035 g, 0.097 mmol) in a mixture of MeOH (1.5 mL) and H2O (1.5 mL) was added LiOH (0.016 g, 0.39 mmol). The resulting mixture was stirred for 2 d at room temp., then was concentrated under reduced pressure. The residue was adjusted to pH 1 with a 1% HCl solution, then extracted with EtOAc (4×10 mL). The combined organic layers were sequentially washed with H2O (15 mL), a saturated NaCl solution (15 mL), and dried (Na2SO4). Concentration under reduced pressure gave (4S)-2-(4-carboxy-2-methylphenylimino)-3,4-diisobutyl-1,3-thiazolidine (0.034 g, 100%): TLC (40% EtOAc/hex) Rf 0.08. This material was used in the next step without further purification.

後処理

  1. concentrationwas concentrated under reduced pressure
  2. extractionextracted with EtOAc (4×10 mL)
  3. washThe combined organic layers were sequentially washed with H2O (15 mL)
  4. dry with materiala saturated NaCl solution (15 mL), and dried (Na2SO4)
  5. concentrationConcentration under reduced pressure

出典と根拠

ORDレコード
ord-08191173ef1345d48ffc6d55a539a27c
出典データセット
uspto-grants-2002_03
特許番号
US06353006B1

反応ノート

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