Trisodium Phosphate → HCID 131724311, compound

HRID 1840439Notes

Reaction equation

HRID 1840439 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:36](=[O:37])[N:6]2[C:7]([C:23]([O:25]CC3C=CC([N+]([O-])=O)=CC=3)=[O:24])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([S:19][CH2:20][CH2:21][OH:22])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].P([O-])([O-])([O-])=O.[Na+:43].[Na+].[Na+].[H][H]>C1COCC1.[Pd]>[OH:1][C@@H:2]([C@H:4]1[C:36](=[O:37])[N:6]2[C:7]([C:23]([O-:25])=[O:24])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([S:19][CH2:20][CH2:21][OH:22])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3].[Na+:43]

Participants

6

Reactant 3

HCID 24243Trisodium PhosphateHCID 91000778HCID 91000778, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131724311HCID 131724311, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-[7-(2-hydroxyethyl)thioimidazo[5,1-b]thiazol-2-yl]-1-methyl-1-carbapen-2-em-3-carboxylate (48.4 mg) was dissolved in 2.5 ml of THF and 2.5 ml of a 1/15 M sodium phosphate buffer (pH 6.6). 10% Pd-C (50 mg) was added to the solution. The air in the reaction vessel was replaced by hydrogen, and the contents of the reaction vessel were stirred at room temperature for 2 hr. The catalyst was removed by filtration on Celite, and was washed with water. The filtrate was washed with ethyl acetate, and was then concentrated under the reduced pressure to bring the volume of the solution to about 1 ml. The residue was purified by column chromatography on Cosmosil 40C18-PREP (20% aqueous methanol solution) to prepare 15.8 mg of the title compound.

Workup

  1. customThe catalyst was removed by filtration on Celite
  2. washwas washed with water
  3. washThe filtrate was washed with ethyl acetate
  4. concentrationwas then concentrated under the reduced pressure
  5. customThe residue was purified by column chromatography on Cosmosil 40C18-PREP (20% aqueous methanol solution)
  6. customto prepare 15.8 mg of the title compound

Sources & evidence

ORD record
ord-d65de5a1152f45f09c37154734229e16
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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