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Hydrochloric Acid → Benzyl (6-oxo-1-(2-oxoethyl)-2-phenyl-1,6-dihydropyrimidin-5-yl)carbamate

HRID 480663
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HRID 480663 반응식
C[O:2][CH:3](OC)[CH2:4][N:5]1[C:10](=[O:11])[C:9]([NH:12][C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[O:14])=[CH:8][N:7]=[C:6]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl>O1CCCC1>[CH2:16]([O:15][C:13]([NH:12][C:9]1[C:10](=[O:11])[N:5]([CH2:4][CH:3]=[O:2])[C:6]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[N:7][CH:8]=1)=[O:14])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 313Hydrochloric AcidHCID 9866209[5-[(Benzyloxycarbonyl)amino]-2-phenyl-6-oxo-1,6-dihydro-1-pyrimidinyl]acetaldehyde dimethyl acetal

생성물 1

HCID 10361338Benzyl (6-oxo-1-(2-oxoethyl)-2-phenyl-1,6-dihydropyrimidin-5-yl)carbamate수율 102.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(EX-1D) A solution of [5-[(benzyloxycarbonyl)amino]-2-phenyl-6-oxo-1,6-dihydro-1-pyrimidinyl]acetaldehyde dimethyl acetal (17.24 g, 42.11 mmol) in 103.0 mL tetrahydrofuran was added 35.0 mL 1 N HCl. The resulting biphasic mixture was allowed to heated to reflux for 12 hours. The reaction mixture was allowed to cool to room temperature and the volatiles were removed under vacuum. The resulting residue was diluted with water (200 mL) and the pH was adjusted to 7 by addition of solid NaHCO3. The resulting emulsion was extracted with dichloromethane (4×150 mL). The combined organic solutions were washed with water (1×200 mL), dried (MgSO4), filtered, and concentrated to give 15.74 g crude [5-[(benzyloxycarbonyl)amino]-2-phenyl-6-oxo-1,6-dihydro-1-pyrimidinyl]acetaldehyde.

후처리

  1. temperatureto heated
  2. temperatureto reflux for 12 hours
  3. customthe volatiles were removed under vacuum
  4. additionThe resulting residue was diluted with water (200 mL)
  5. additionthe pH was adjusted to 7 by addition of solid NaHCO3
  6. extractionThe resulting emulsion was extracted with dichloromethane (4×150 mL)
  7. washThe combined organic solutions were washed with water (1×200 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0d5c0e7ceb284e5bbbdbfbd80b0a810d
출처 데이터셋
uspto-grants-2003_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06653316B1

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