HCID 12804816, compound → HCID 12805476, compound

HRID 258426Notes

Reaction equation

HRID 258426 reaction equation
S1C2C=CC=CC=2N=C1S[S:11][C@H:12]1[N:15]([CH:16]([C:33]([CH3:35])=[CH2:34])[C:17]([O:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])[C:14](=[O:36])[C@H:13]1[NH:37][C:38](=[O:47])[CH2:39][O:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.O.[C:49]1([CH3:58])[CH:54]=[CH:53][C:52]([S:55]([O-:57])=[O:56])=[CH:51][CH:50]=1.[Na+]>CC(C)=O.O.[N+]([O-])([O-])=O.[Ag+]>[C:49]1([CH3:58])[CH:54]=[CH:53][C:52]([S:55]([S:11][C@H:12]2[N:15]([CH:16]([C:33]([CH3:35])=[CH2:34])[C:17]([O:19][CH:20]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)=[O:18])[C:14](=[O:36])[C@H:13]2[NH:37][C:38](=[O:47])[CH2:39][O:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)(=[O:57])=[O:56])=[CH:51][CH:50]=1

Participants

6

Reactant 2

HCID 12804816HCID 12804816, compoundHCID 236829571011708-74-9

Product 1

HCID 12805476HCID 12805476, compoundYield 74.1%

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent3×HCID 962WaterSolvent2×

Procedure

To a solution of diphenylmethyl 2-[(3R,4R)-4-[(benzothiazol-2-yl)dithio]-3-phenoxyacetamido-2-oxo-azetidin-1-yl]-3-methyl-3-butenoate (XIIIa. 12.12 g, 0.0182 mole) in acetone (325 mL) and water (37 mL), silver nitrate (3.86 g, 0.0227 mole) was added all at once. A freshly prepared solution of sodium p-toluenesulfinate hydrate (4.05 g; 0.0227 mole) in acetone (255 mL) and water (37 mL) was added dropwise over 1 h, while the reaction mixture was protected from light. After an additional 1h period at room temperature, Celite (5 g) was added and the mixture was diluted with acetone (500 mL) and then was filtered. The filtrate was evaporated to a small volume, and the crude product was extracted into ether (3×250 mL). The ether phase was dried with magnesium sulfate and concentrated to afford a crude product. Flash chromatography (SiO2, eluting with 40% ethyl acetate in hexane) gave 9.05 g (73.5%) of the title compound as a white solid.

Workup

  1. filtrationwas filtered
  2. customThe filtrate was evaporated to a small volume
  3. extractionthe crude product was extracted into ether (3×250 mL)
  4. dry with materialThe ether phase was dried with magnesium sulfate
  5. concentrationconcentrated
  6. customto afford a crude product
  7. washFlash chromatography (SiO2, eluting with 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8d4c6a772b084f35beba24f23dfdd98d
Source dataset
uspto-grants-1993_11
Patent number
US05266691

Reaction notes

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