Acetic Acid → HCID 14230819, compound

HRID 1759231Notes

Reaction equation

HRID 1759231 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15]([S:16][C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18])[N:14]([C:25](=[O:36])[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[C:13]1=[O:37])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>O1CCCC1.C(Cl)Cl.O>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15]([S:16][C:17]([O:19][CH2:20][C:21]([Cl:24])([Cl:23])[Cl:22])=[O:18])[N:14]([CH:25]([OH:36])[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[C:13]1=[O:37])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 14230818HCID 14230818, compound

Product 1

HCID 14230819HCID 14230819, compoundYield 101%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzyl [3-phenoxyacetamido-4-(2,2,2-trichloroethoxycarbonylthio)-2-oxo-1-azetidinyl]glyoxylate (7.5 g.) and acetic acid (2.28 ml.) in tetrahydrofuran (30 ml.) was added portionwise sodium borohydride (480 mg.) over a period of half an hour at 0° C. After stirring for 10 minutes, the reaction mixture was diluted with methylene chloride (50 ml.), poured into a mixture of sodium bicarbonate (6.0 g.) in water (80 ml.) and a saturated aqueous solution of sodium chloride (20 ml.), and then extracted with methylene chloride (100 ml.). The extract was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and then filtered through a pad of Celite. Removal of the solvent gave an amorphous solid (7.60 g.) of benzyl 2-[3-phenoxyacetamido-4-(2,2,2-trichloroethoxycarbonylthio)-2-oxo-1-azetidinyl]-2-hydroxyacetate.

Workup

  1. extractiona saturated aqueous solution of sodium chloride (20 ml.), and then extracted with methylene chloride (100 ml.)
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered through a pad of Celite
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-ec7fdb1b2561491aa468c75775519d7c
Source dataset
uspto-grants-1982_07
Patent number
US04339449

Reaction notes

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