Hydrochloric Acid → HCID 11852764, compound

HRID 2246166Notes

Reaction equation

HRID 2246166 reaction equation
Cl.[OH:2][C@@H:3]([C@H:5]1[C:25](=[O:26])[N:7]2[C:8]([C:22]([O-:24])=[O:23])=[C:9]([S:12]/[CH:13]=[CH:14]\[C:15]3[S:19][CH:18]=[N:17][C:16]=3[CH2:20][OH:21])[C@H:10]([CH3:11])[C@H:6]12)[CH3:4].[Na+]>>[OH:2][C@@H:3]([C@H:5]1[C:25](=[O:26])[N:7]2[C:8]([C:22]([OH:24])=[O:23])=[C:9]([S:12]/[CH:13]=[CH:14]\[C:15]3[S:19][CH:18]=[N:17][C:16]=3[CH2:20][OH:21])[C@H:10]([CH3:11])[C@H:6]12)[CH3:4]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 23676797Sodium (1r,5s,6s)-6-((1r)-1-hydroxyethyl)-2-[[(z)-2-(4-hydroxymethyl-thiazol-5-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylate

Product 1

HCID 11852764HCID 11852764, compoundYield 63.1%

Procedure

1 N Hydrochloric acid (7.10 ml) was added to 120 ml of an aqueous solution of 2.73 g of sodium (1R,5S,6S)-6-((1R)-1-hydroxyethyl)-2-[[(Z)-2-(4-hydroxymethylthiazol-5-yl)ethen-1-yl]thio]-1-methyl-1-carbapen-2-em-3-carboxylate at room temperature, and the mixture was stirred for 3 min. The reaction mixture was extracted twice with 150 ml of ethyl acetate. The extract was dried over anhydrous magnesium sulfate and was filtered, and ethyl acetate was removed by distillation under the reduced pressure until the amount of ethyl acetate was reduced to 50 ml. Hexane (200 ml) was added, and the precipitated solid was collected by filtration to give 1.63 g of the title compound.

Workup

  1. extractionThe reaction mixture was extracted twice with 150 ml of ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. filtrationwas filtered
  4. customethyl acetate was removed by distillation under the reduced pressure until the amount of ethyl acetate
  5. additionHexane (200 ml) was added
  6. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-495bd45c81934ad6bfb58aeb94171718
Source dataset
uspto-grants-2010_03
Patent number
US07687490B2

Reaction notes

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