HCID 131725360, compound → HCID 58595198, compound

HRID 891542Notes

Reaction equation

HRID 891542 reaction equation
[N+](C1C=CC(COC([N:12]2[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([C:20]3[N:21]=[C:22]([N:25]4[CH2:28][CH:27]([S:29][C:30]5[C@H:31]([CH3:54])[C@@H:32]6[C@@H:49]([C@H:50]([OH:52])[CH3:51])[C:48](=[O:53])[N:33]6[C:34]=5[C:35]([O:37]CC5C=CC([N+]([O-])=O)=CC=5)=[O:36])[CH2:26]4)[O:23][CH:24]=3)=[O:19])[CH2:13]2)=O)=CC=1)([O-])=O>O1CCCC1>[NH:12]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18]([C:20]2[N:21]=[C:22]([N:25]3[CH2:28][CH:27]([S:29][C:30]4[C@H:31]([CH3:54])[C@@H:32]5[C@@H:49]([C@H:50]([OH:52])[CH3:51])[C:48](=[O:53])[N:33]5[C:34]=4[C:35]([OH:37])=[O:36])[CH2:26]3)[O:23][CH:24]=2)=[O:19])[CH2:13]1

Participants

3

Reactant 1

HCID 131725360HCID 131725360, compound

Product 1

HCID 58595198HCID 58595198, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

p-Nitrobenzyl (1R,5S,6S)-2-(1-{4-[(3S)-1-(p-nitrobenzyloxycarbonyl)-pyrrolidin-3-ylcarbamoyl]-1,3-oxazol-2-yl}azetidin-3-yl)thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (650 mg, 0.821 mmol) (obtained as described in Example 80(1)) in a mixture of tetrahydrofuran (33 ml) and distilled water (33 ml) was subjected to catalytic hydrogenation in the presence of 10% palladium on charcoal (650 mg) at room temperature for 4.5 hours. After checking the completion of the reaction, the reaction mixture was filtered and to the filtrate were added ethyl acetate and distilled water. The resulting mixture was shaken in a separatory funnel and the aqueous layer was separated and concentrated under reduced pressure. The residue was purified by chromatography on a Cosmosil column (eluant: distilled water distilled water:acetonitrile (76:24)),and the eluate was lyophilized to afford the desired compound (1R,5S,6S)-2-{1-[4-((3S)-pyrrolidin-3-ylcarbamoyl)-1,3-oxazol-2-yl]azetidin-3-yl}thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid (129 mg, yield 33%) as a white solid.

Workup

  1. distillationdistilled water (33 ml)
  2. customthe completion of the reaction
  3. filtrationthe reaction mixture was filtered and to the filtrate
  4. additionwere added ethyl acetate
  5. distillationdistilled water
  6. customthe aqueous layer was separated
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by chromatography on a Cosmosil column (eluant
  9. distillationdistilled water
  10. distillationdistilled water

Sources & evidence

ORD record
ord-2fc878e7aeb9400fade5abb517ccaa6a
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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