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

HRID 1352820노트

반응식

HRID 1352820 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e4970f9a9b1047c58a458993bc01efc2
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07220780B2

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