HCID 12912424, compound → HCID 54435877, compound

HRID 258427Notes

Reaction equation

HRID 258427 reaction equation
S1C2C=CC=CC=2N=C1S[S:11][C@H:12]1[N:15]([CH:16]([C:30]([CH3:32])=[CH2:31])[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[O:18])[C:14](=[O:33])[C@H:13]1[NH:34][C:35](=[O:44])[CH2:36][O:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.O.[C:46]1([CH3:55])[CH:51]=[CH:50][C:49]([S:52]([O-:54])=[O:53])=[CH:48][CH:47]=1.[Na+]>CC(C)=O.O.[N+]([O-])([O-])=O.[Ag+]>[C:46]1([CH3:55])[CH:51]=[CH:50][C:49]([S:52]([S:11][C@H:12]2[N:15]([CH:16]([C:30]([CH3:32])=[CH2:31])[C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=3)=[O:18])[C:14](=[O:33])[C@H:13]2[NH:34][C:35](=[O:44])[CH2:36][O:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)(=[O:54])=[O:53])=[CH:48][CH:47]=1

Participants

6

Reactant 2

HCID 12912424HCID 12912424, compoundHCID 236829571011708-74-9

Product 1

HCID 54435877HCID 54435877, compound

Reagents, catalysts & solvents 3

HCID 24470Silver NitrateCatalystHCID 180AcetoneSolvent2×HCID 962WaterSolvent2×

Procedure

A suspension of 4-nitrobenzyl 2-[(3R,4R)-4-[(benzothiazol-2-yl)dithio]-3-phenoxyacetamido-2-oxo-azetidin-1-yl]-3-methyl-3-butenoate (XIIIc, 3.25 g, 0.005 mole) in acetone (90 mL) and water (10 mL) was treated at room temperature with silver nitrate (1.06 g, 0.00625 mole), followed by treatment with a solution of sodium p-toluenesulfinate hydrate (0.90 g, 0.050 mole) in acetone (70 mL) - water (10 mL). The slurry was stirred for 1 h at room temperature under darkness. It was then filtered through Celite, which was washed with acetone. The volume of the filterate was reduced in vacuo, and the product was extracted into ether (3×250 mL). The ether phase was dried over magnesium sulfate and concentrated. Flash chromatography (silica gel, 50% ethyl acetate in hexane) gave the pure title product, XIIId, as a solid (2.053 g, 62%).

Workup

  1. filtrationIt was then filtered through Celite, which
  2. washwas washed with acetone
  3. extractionthe product was extracted into ether (3×250 mL)
  4. dry with materialThe ether phase was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9aee73861e214a2dbb111ae1ed8ece4c
Source dataset
uspto-grants-1993_11
Patent number
US05266691

Reaction notes

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