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3-{4-[4-(Tert-butoxycarbonylaminocarboxymethyl)-phenoxy]-phenyl}-acrylic acid methyl ester → 3-{4-[4-(Tert-butoxycarbonylaminocarboxymethyl)-phenoxy]-phenyl}-propionic acid methyl ester

HRID 749002
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HRID 749002 반응식
[CH3:1][O:2][C:3](=[O:31])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([NH:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:20]([OH:22])=[O:21])=[CH:15][CH:14]=2)=[CH:8][CH:7]=1.[H][H]>[Ni].CO>[CH3:1][O:2][C:3](=[O:31])[CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][C:13]2[CH:18]=[CH:17][C:16]([CH:19]([NH:23][C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[C:20]([OH:22])=[O:21])=[CH:15][CH:14]=2)=[CH:10][CH:11]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 692266383-{4-[4-(Tert-butoxycarbonylaminocarboxymethyl)-phenoxy]-phenyl}-acrylic acid methyl esterHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 597511053-{4-[4-(Tert-butoxycarbonylaminocarboxymethyl)-phenoxy]-phenyl}-propionic acid methyl ester수율 75.1%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 887Methanol
용매

실험 절차

Raney nickel 2800 (21.9 g) was added to a degassed solution of the unsaturated ester 30 (20.0 g) in MeOH (100 mL) and the resulting suspension was treated with hydrogen at atmospheric pressure for 18 h. The suspension was filtered over a Celite® bed and concentrated. Completion of hydrogenation was determined by NMR. Flash chromatography (20-50% ethyl acetate in hexane containing 1% acetic acid) of the resulting residue gave the desired saturated ester 31 (15.1 g, 75%). 1H NMR (400 MHz, DMSO-d6): 12.8 (br, 1H), 7.37 (d, J=8.8 Hz, 2H), 7.24 (d, J=8.4 Hz, 2H), 6.93 (d, J=8.4 Hz, 4H), 3.59 (s, 3H), 2.84 (t, J=7.6 Hz, 2H), 2.63 (t, J=7.6 Hz, 2H) 1.39 (s, 9H).

후처리

  1. filtrationThe suspension was filtered over a Celite® bed
  2. concentrationconcentrated

출처 및 근거

ORD 기록
ord-87b16f5e3b7748498a2bfae7e5f6d803
출처 데이터셋
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07399786B2

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