HCID 131725338, compound → HCID 58595181, compound

HRID 891521Notes

Reaction equation

HRID 891521 reaction equation
[N+](C1C=CC(COC([N:12]2[CH2:15][CH:14]([NH:16][C:17]([C:19]3[N:20]=[C:21]([N:24]4[CH2:27][CH:26]([S:28][C:29]5[C@H:30]([CH3:53])[C@@H:31]6[C@@H:48]([C@H:49]([OH:51])[CH3:50])[C:47](=[O:52])[N:32]6[C:33]=5[C:34]([O:36]CC5C=CC([N+]([O-])=O)=CC=5)=[O:35])[CH2:25]4)[S:22][CH:23]=3)=[O:18])[CH2:13]2)=O)=CC=1)([O-])=O>O1CCCC1>[NH:12]1[CH2:15][CH:14]([NH:16][C:17]([C:19]2[N:20]=[C:21]([N:24]3[CH2:27][CH:26]([S:28][C:29]4[C@H:30]([CH3:53])[C@@H:31]5[C@@H:48]([C@H:49]([OH:51])[CH3:50])[C:47](=[O:52])[N:32]5[C:33]=4[C:34]([OH:36])=[O:35])[CH2:25]3)[S:22][CH:23]=2)=[O:18])[CH2:13]1

Participants

3

Reactant 1

HCID 131725338HCID 131725338, compound

Product 1

HCID 58595181HCID 58595181, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

p-Nitrobenzyl (1R,5S,6S)-2-(1-{4-[1-(p-nitrobenzyloxycarbonyl)-azetidin-3-ylcarbamoyl]-1,3-thiazol-2-yl}azetidin-3-yl)thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylate (490 mg, 0.617 mmol) (obtained as described in Example 59(1)) in a mixture of tetrahydrofuran (25 ml) and distilled water (25 ml) was subjected to catalytic hydrogenation in the presence of 20% palladium hydroxide on charcoal (490 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-(azetidin-3-ylcarbamoyl)-1,3-thiazol-2-yl]azetidin-3-yl}thio-6-[(R)-1-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid (143 mg, yield 49%) as a white solid.

Workup

  1. distillationdistilled water (25 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-1d892f07a97444c6b10f0e4b04128e31
Source dataset
uspto-grants-2006_02
Patent number
US07001897B2

Reaction notes

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