HCID 131725336, compound → HCID 58595154, compound

HRID 891517Notes

Reaction equation

HRID 891517 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)[S: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)[S:23][CH:24]=2)=[O:19])[CH2:13]1

Participants

3

Reactant 1

HCID 131725336HCID 131725336, compound

Product 1

HCID 58595154HCID 58595154, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

p-Nitrobenzyl (1R,5S,6S)-2-(1-{4-[(3S)-1-(p-nitrobenzyloxycarbonyl)-pyrrolidin-3-ylcarbamoyl]-1,3-thiazol-2-yl}azetidin-3-yl)thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (390 mg, 0.483 mmol) (obtained as described in Example 57(1)) in a mixture of tetrahydrofuran (20 ml) and distilled water (20 ml) was subjected to catalytic hydrogenation in the presence of 20% palladium hydroxide on charcoal (390 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 mixture was shaken in a separatory funnel. 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-thiazol-2-yl]azetidin-3-yl}thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid (90 mg, yield 38%) as a white solid.

Workup

  1. distillationdistilled water (20 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 (76:24))

Sources & evidence

ORD record
ord-c41b2d1884094cb7901ba1d95563c519
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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