3-Benzyloxy-1-[(phenylbenzylcarbamoyl)methyl]-2-(1H)-pyridinone → 3-Hydroxy-1-[(phenylbenzylcarbamoyl)methyl]-2-(1H)-pyridinone

HRID 2106062노트

반응식

HRID 2106062 반응식
C([O:8][C:9]1[C:10](=[O:32])[N:11]([CH2:15][C:16](=[O:31])[N:17]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[H][H]>CCO.[Pd]>[OH:8][C:9]1[C:10](=[O:32])[N:11]([CH2:15][C:16](=[O:31])[N:17]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:12]=[CH:13][CH:14]=1

참가 물질

5

반응물 2

HCID 667463123-Benzyloxy-1-[(phenylbenzylcarbamoyl)methyl]-2-(1H)-pyridinoneHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 673739623-Hydroxy-1-[(phenylbenzylcarbamoyl)methyl]-2-(1H)-pyridinone수율 22%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매2회

실험 절차

18 (280 mg, 0.7 mmol) was suspended in 150 mL of EtOH. 10% (w/w, 38 mg) of 10% Pd/C catalyst was added to the hydrogenation flask (500 mL Pyrex® Parr reaction bottle tested to 120 psi, max. working pressure of 60 psi). The hydrogen pressure was set to 35 psi with agitation, and the process went on for 19 h. The catalyst was removed by vacuum filtration and separated from the product by dissolving the white precipitate in 100 mL hot CH2Cl2. An additional batch of product was isolated by cooling the EtOH filtrate to 0° C. for 2 h. The clear solution was concentrated by rotary evaporation to yield a white solid. The solid was washed with MeOH to remove residual DCU. Yield: 22%. 1H NMR (d6-DMSO, 400 MHz, 25° C.): δ 4.34 (d, J=6.0 Hz, 2H, —CH2—), 4.63 (s, 2H, —CH2—), 6.08 (t, J=7.2 Hz, 1H, Ar—H), 6.69 (d, J=7.2 Hz, 1H, Ar—H), 7.10 (d, J=6.4 Hz, 1H, Ar—H), 7.44 (m, 5H, Bz—H), 7.64 (m, 4H, Phenyl-H), 8.70 (t, J=5.6 Hz, 1H, —NH—), 9.02 (s, 1H, —OH). APCI-MS: m/z 334.9 [M+H]+. Anal. Calcd for C20H18N2O3: C, 71.84; H, 5.43; N, 8.38. Found: C, 71.49; H, 5.78; N, 8.52.

후처리

  1. customwent on for 19 h
  2. customThe catalyst was removed by vacuum filtration
  3. customseparated from the product
  4. dissolutionby dissolving the white precipitate in 100 mL hot CH2Cl2
  5. customAn additional batch of product was isolated
  6. concentrationThe clear solution was concentrated by rotary evaporation
  7. customto yield a white solid
  8. washThe solid was washed with MeOH
  9. customto remove residual DCU

출처 및 근거

ORD 기록
ord-27a40722dcfd4e24b04565cfb3081a22
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07579486B2

반응 노트

불러오는 중…