HCID 131725335, compound → HCID 58595103, compound

HRID 891515Notes

Reaction equation

HRID 891515 reaction equation
[N+](C1C=CC(COC([N:12]2[CH2:17][CH2:16][CH:15]([NH:18][C:19]([C:21]3[N:22]=[C:23]([N:26]4[CH2:29][CH:28]([S:30][C:31]5[C@H:32]([CH3:55])[C@@H:33]6[C@@H:50]([C@H:51]([OH:53])[CH3:52])[C:49](=[O:54])[N:34]6[C:35]=5[C:36]([O:38]CC5C=CC([N+]([O-])=O)=CC=5)=[O:37])[CH2:27]4)[S:24][CH:25]=3)=[O:20])[CH2:14][CH2:13]2)=O)=CC=1)([O-])=O>O1CCCC1>[NH:12]1[CH2:13][CH2:14][CH:15]([NH:18][C:19]([C:21]2[N:22]=[C:23]([N:26]3[CH2:27][CH:28]([S:30][C:31]4[C@H:32]([CH3:55])[C@@H:33]5[C@@H:50]([C@H:51]([OH:53])[CH3:52])[C:49](=[O:54])[N:34]5[C:35]=4[C:36]([OH:38])=[O:37])[CH2:29]3)[S:24][CH:25]=2)=[O:20])[CH2:16][CH2:17]1

Participants

3

Reactant 1

HCID 131725335HCID 131725335, compound

Product 1

HCID 58595103HCID 58595103, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

p-Nitrobenzyl (1R,5S,6S)-2-(1-{4-[1-(p-nitrobenzyloxycarbonyl)-piperidin-4-ylcarbamoyl]-1,3-thiazol-2-yl}azetidin-3-yl)thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (340 mg, 0.414 mmol) (obtained as described in Example 56(1)) in a mixture of tetrahydrofuran (17 ml) and distilled water (17 ml) was subjected to catalytic hydrogenation in the presence of 10% palladium on charcoal (340 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 (8:2)) and the eluate was lyophilized to afford the desired compound (1R,5S,6S)-2-{1-[4-(piperidin-4-ylcarbamoyl)-1,3-thiazol-2-yl]azetidin-3-yl}thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid (70 mg, yield 33%) as a white solid.

Workup

  1. distillationdistilled water (17 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 (8:2))

Sources & evidence

ORD record
ord-85fae05a572642f584329ef20dacc911
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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