HCID 131725361, compound → HCID 58595058, compound

HRID 891543Notes

Reaction equation

HRID 891543 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 131725361HCID 131725361, compound

Product 1

HCID 58595058HCID 58595058, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

p-Nitrobenzyl (1R,5S,6S)-2-{1-[4-((3R)-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 (320 mg, 0.404 mmol) (obtained as described in Example 81(1)) in a mixture of tetrahydrofuran (16 ml) and distilled water (16 ml) was subjected to catalytic hydrogenation in the presence of 10% palladium on charcoal (320 mg) at room temperature for 4 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 (79:21)) and the eluate was lyophilized to afford the desired compound (1R,5S,6S)-2-{1-[4-((3R)-pyrrolidin-3-ylcarbamoyl)-1,3-oxazol-2-yl]azetidin-3-yl}thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid (88 mg, yield 46%) as a white solid.

Workup

  1. distillationdistilled water (16 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. distillationThe residue was purified by chromatography on a Cosmosil column (eluant: distilled water→distilled water:acetonitrile (79:21))

Sources & evidence

ORD record
ord-1a157b4998574be0b79cf29dd2c8e735
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

Loading…