Water → Ertapenem

HRID 2067708Notes

Reaction equation

HRID 2067708 reaction equation
[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]

Participants

7

Reactant 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

Product 1

HCID 150610Ertapenem

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-74a0627d0e6644a7bd9fc3bf79cda160
Source dataset
uspto-grants-2012_10
Patent number
US08293894B2

Reaction notes

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