Trisodium Phosphate → HCID 91079210, compound

HRID 1840440Notes

Reaction equation

HRID 1840440 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:37](=[O:38])[N:6]2[C:7]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=3)=[O:25])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([S:19]([CH2:21][CH2:22][OH:23])=[O:20])[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:40].[Na+].[Na+].[Na+].[H][H]>C1COCC1.[Pd]>[OH:1][C@@H:2]([C@H:4]1[C:37](=[O:38])[N:6]2[C:7]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=3)=[O:25])=[C:8]([C:11]3[S:15][C:14]4=[C:16]([S:19]([CH2:21][CH2:22][OH:23])(=[O:40])=[O:20])[N:17]=[CH:18][N:13]4[CH:12]=3)[C@H:9]([CH3:10])[C@H:5]12)[CH3:3]

Participants

6

Reactant 3

HCID 24243Trisodium PhosphateHCID 91261716HCID 91261716, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 91079210HCID 91079210, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

4-Nitrobenzyl (1S,5R,6S)-6-((1R)-1-hydroxyethyl)-2-[7-(2-hydroxyethyl)sulfinylimidazo[5,1-b]thiazol-2-yl]-1-methyl-1-carbapen-2-em-3-carboxylate (a mixture of diastereomers) (50.1 mg) was dissolved in 1.8 ml of THF and 1.8 ml of a 1/15 M sodium phosphate buffer (pH 6.6). 10% Pd-C (54.7 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 50 min. The catalyst was removed by filtration on Celite, and was washed with water. The filtrate was adjusted to pH 7.0 by the addition of an aqueous sodium hydrogencarbonate solution, and was then washed with ethyl acetate. The aqueous layer was then purified by column chromatography on Cosmosil 40C18-PREP (only water) to prepare 21.4 mg of the title compound.

Workup

  1. customThe catalyst was removed by filtration on Celite
  2. washwas washed with water
  3. additionThe filtrate was adjusted to pH 7.0 by the addition of an aqueous sodium hydrogencarbonate solution
  4. washwas then washed with ethyl acetate
  5. customThe aqueous layer was then purified by column chromatography on Cosmosil
  6. custom(only water) to prepare 21.4 mg of the title compound

Sources & evidence

ORD record
ord-ebc5aa81b9c04e86a5daeffeff4cd4f7
Source dataset
uspto-grants-2004_01
Patent number
US06680313B2

Reaction notes

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