HCID 131725337, compound → HCID 58595176, compound

HRID 891519Notes

Reaction equation

HRID 891519 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 131725337HCID 131725337, compound

Product 1

HCID 58595176HCID 58595176, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

p-Nitrobenzyl (1R,5S,6S)-2-(1-{4-[(3R)-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 (410 mg, 0.508 mmol) (obtained as described in Example 58(1)) in a mixture of tetrahydrofuran (21 ml) and distilled water (21 ml) was subjected to catalytic hydrogenation in the presence of 20% palladium hydroxide on charcoal (410 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, washed with the above-mentioned mixed solvent 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-((3R)-pyrrolidin-3-ylcarbamoyl)-1,3-thiazol-2-yl]azetidin-3yl}thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid (101 mg, yield 41%) as a white solid.

Workup

  1. distillationdistilled water (21 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. washwashed with the above-mentioned mixed solvent
  8. concentrationconcentrated under reduced pressure
  9. distillationThe residue was purified by chromatography on a Cosmosil column (eluant: distilled water→distilled water:acetonitrile (76:24))

Sources & evidence

ORD record
ord-8cdfa2a660ac4057be9b9e499d67a03f
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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