(S)-[1-[[[[3-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester → (S)-N-[3-[[[(3-Amino-2-oxo-1-azetidinyl)carbonyl]amino]-sulfonyl]tetrahydro-2-oxo-1(2H)-pyrimidinyl]-1,4-dihydro-5-hydroxy-4-oxo-2-pyridinecarboxamide

HRID 2351087노트

반응식

HRID 2351087 반응식
[OH:1][C:2]1[C:3](=[O:40])[CH:4]=[C:5]([C:8]([NH:10][N:11]2[CH2:16][CH2:15][CH2:14][N:13]([S:17]([NH:20][C:21]([N:23]3[CH2:26][C@H:25]([NH:27]C(=O)OCC4C=CC=CC=4)[C:24]3=[O:38])=[O:22])(=[O:19])=[O:18])[C:12]2=[O:39])=[O:9])[NH:6][CH:7]=1>CN(C)C=O.[Pd]>[NH2:27][C@H:25]1[CH2:26][N:23]([C:21]([NH:20][S:17]([N:13]2[CH2:14][CH2:15][CH2:16][N:11]([NH:10][C:8]([C:5]3[NH:6][CH:7]=[C:2]([OH:1])[C:3](=[O:40])[CH:4]=3)=[O:9])[C:12]2=[O:39])(=[O:18])=[O:19])=[O:22])[C:24]1=[O:38]

참가 물질

4

반응물 1

HCID 86743424(S)-[1-[[[[3-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester

생성물 1

HCID 53731386(S)-N-[3-[[[(3-Amino-2-oxo-1-azetidinyl)carbonyl]amino]-sulfonyl]tetrahydro-2-oxo-1(2H)-pyrimidinyl]-1,4-dihydro-5-hydroxy-4-oxo-2-pyridinecarboxamide

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 6228Dimethylformamide용매

실험 절차

4.95 g (8.57 mmol) (S)-[1-[[[[3-[[(1,4-dihydro-5-hydroxy-4-oxo-2-pyridinyl)-carbonyl]amino]tetrahydro-2-oxo-1(2H)-pyrimidinyl]sulfonyl]amino]carbonyl]-2-oxo-3-azetidinyl]carbamic acid, phenylmethyl ester was dissolved in 50 ml N,N-dimethylformamide. After the addition of 2.5 g palladium on carbon, the mixture was hydrogenated for 1 hour. The catalyst was removed and subsequently the filtrate added dropwise to 500 ml isopropanol. The desired product was filtered off, slurried with either and dried in vacuo. Yield 3.03 g, melting range 160°-220° C. (dec.).

후처리

  1. customThe catalyst was removed
  2. additionsubsequently the filtrate added dropwise to 500 ml isopropanol
  3. filtrationThe desired product was filtered off
  4. customdried in vacuo

출처 및 근거

ORD 기록
ord-1506582b737344328de7790582027360
출처 데이터셋
uspto-grants-1989_10
특허 번호
US04871841

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