Water → Ertapenem

HRID 2067708노트

반응식

HRID 2067708 반응식
[SH:1][C@@H:2]1[CH2:6][N:5](C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[C@H:4]([C:20]([NH:22][C:23]2[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=2)[C:26]([OH:28])=[O:27])=[O:21])[CH2:3]1.[OH:32][C@@H:33]([C@H:35]1[C:72](=[O:73])[N:37]2[C:38]([C:59]([O:61]CC3C=CC([N+]([O-])=O)=CC=3)=[O:60])=[C:39](OP(OC3C=CC=CC=3)(OC3C=CC=CC=3)=O)[C@H:40]([CH3:41])[C@H:36]12)[CH3:34].C(N(CC)C(C)C)(C)C.O>CN(C=O)C.C(OCC)(=O)C>[CH3:41][C@H:40]1[C:39]([S:1][C@@H:2]2[CH2:6][NH:5][C@H:4]([C:20]([NH:22][C:23]3[CH:31]=[CH:30][CH:29]=[C:25]([C:26]([OH:28])=[O:27])[CH:24]=3)=[O:21])[CH2:3]2)=[C:38]([C:59]([OH:61])=[O:60])[N:37]2[C@H:36]1[C@@H:35]([C@H:33]([OH:32])[CH3:34])[C:72]2=[O:73]

참가 물질

7

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 10304013(4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylateHCID 154092601-[(4-Nitrophenyl)methyl] (2S,4S)-2-[[(3-carboxyphenyl)amino]carbonyl]-4-mercapto-1-pyrrolidinecarboxylate

생성물 1

HCID 150610Ertapenem

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To 3-[[[(2S,4S)-4-mercapto-1-(4-nitrobenzyloxy)carbonyl-2-pyrrolidinyl]carbonyl]amino]benzoic acid (7.68 g) in DMF (30 mL), p-nitrobenzyl (1R,5R,6S)-6-[(1R)-1-hydroxyethyl]-2-[(diphenylphosphono)oxy]-1-methylcarbapen-2em-3-carboxylate (10 g) was added. To the reaction mixture N,N-diisopropylethylamine (4.78 g) was added at −30° C. and stirred. After completion of reaction, the reaction mass was poured into water and ethyl acetate mixture at 10° C. The layers were separated and organic layer washed with brine solution. The organic layer was subjected to carbon treatment and taken for subsequent step.

후처리

  1. customAfter completion of reaction
  2. customThe layers were separated
  3. washorganic layer washed with brine solution

출처 및 근거

ORD 기록
ord-74a0627d0e6644a7bd9fc3bf79cda160
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293894B2

반응 노트

불러오는 중…