Trifluoroacetic acid → 3-Carboxy-5-(1,1-dimethylethyl)-alpha-(3-mercaptopropyl)-benzenepropanoic acid

HRID 1352820ノート

反応式

HRID 1352820 の反応式
[C:1]([C:5]1[CH:6]=[C:7]([CH:36]=[C:37]([C:39]([O:41]C)=[O:40])[CH:38]=1)[CH2:8][CH:9]([CH2:13][CH2:14][CH2:15][S:16]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:10]([OH:12])=[O:11])([CH3:4])([CH3:3])[CH3:2].C([SiH](C(C)C)C(C)C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:39]([C:37]1[CH:36]=[C:7]([CH2:8][CH:9]([CH2:13][CH2:14][CH2:15][SH:16])[C:10]([OH:12])=[O:11])[CH:6]=[C:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[CH:38]=1)([OH:41])=[O:40]

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 138754Silane, tris(1-methylethyl)-HCID 121446632-(3-Tert-butyl-5-methoxycarbonyl-benzyl)-5-[(triphenylmethyl)thio]-pentanoic acid

生成物 1

HCID 98402473-Carboxy-5-(1,1-dimethylethyl)-alpha-(3-mercaptopropyl)-benzenepropanoic acid収率 55%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-(3-tert-butyl-5-methoxycarbonyl-benzyl)-5-[(triphenylmethyl)thio]pentanoic acid XII (5.5 g, 9.7 mmol) in dichloromethane (30 mL) were added triisopropylsilane (2.4 mL, 11.6 mmol) and trifluoroacetic acid (10 mL), and the mixture was stirred at room temperature for 10 minutes. The solvent was removed under reduced pressure and the crude material was purified by silica gel chromatography (1% AcOH in Hexanes/EtOAc, 4:1) to afford 3-carboxy-5-(1,1-dimethylethyl)-alpha-(3-mercaptopropyl)-benzenepropanoic acid (1.7 g, 5.3 mmol, 55%) as a white solid: 1H NMR (CD3OD) δ1.3 (s, 9H), 1.5-1.8 (m, 4H), 2.4 (m, 2H), 2.6-2.7 (m, 1H), 2.8-2.9 (m, 1H), 2.9-3.0 (m, 1H), 7.5 (s, 1H), 7.7 (s, 1H), 7.8 (s, 1H); 13C NMR (CD3OD) δ24.8, 31.7 (3C), 31.9, 32.9, 35.6, 39.5, 48.6, 125.7, 128.5, 131.6, 132.0, 140.9, 152.8, 170.3, 179.0. Elemental analysis calculated for C17H24O4S: C, 62.93; H, 7.46; S, 9.88. Found: C, 63.02; H, 7.36; S, 9.82.

後処理

  1. customThe solvent was removed under reduced pressure
  2. customthe crude material was purified by silica gel chromatography (1% AcOH in Hexanes/EtOAc, 4:1)

出典と根拠

ORDレコード
ord-e4970f9a9b1047c58a458993bc01efc2
出典データセット
uspto-grants-2007_05
特許番号
US07220780B2

反応ノート

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