HCID 12804816, compound → HCID 12805476, compound

HRID 373328Notes

Reaction equation

HRID 373328 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 1 h period at room temperature, Celite (5g) 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-93d12be56f124085b38a54ed2e1e83f2
Source dataset
uspto-grants-1992_11
Patent number
US05162524

Reaction notes

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