Ethyl Acetate → HCID 53866326, compound

HRID 1701670Notes

Reaction equation

HRID 1701670 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH2:15][N:14]([C:16](=[C:33]([CH3:36])[CH2:34]Br)[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:13]1=[O:37])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:38](OCC)(=[O:40])C.O(CC(NC1CN(C(OC)(C(C)=C)C(OC(C2C=CC=CC=2)C2C=CC=CC=2)=O)C1=O)=O)C1C=CC=CC=1>CO.Cl([O-])(=O)(=O)=O.[Ag+]>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH2:15][N:14]([C:16](=[C:33]([CH3:36])[CH2:34][O:40][CH3:38])[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:13]1=[O:37])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 54338949HCID 54338949, compoundHCID 54357627HCID 54357627, compound

Product 1

HCID 53866326HCID 53866326, compound

Reagents, catalysts & solvents 2

HCID 24562Silver perchlorateCatalystHCID 887MethanolSolvent

Procedure

To a solution of 281 mg (0.5 mmol) of benzhydryl 2-(3-phenoxyacetamido-2-oxoazetidin-1-yl)-3-methyl-4-bromo-2-butenoate in 10 ml of methanol at 0° was added 207 mg (1 mmol) of silver perchlorate. The reaction mixture was stirred for 1 hour. A large amount of ethyl acetate was added. The resulting solution was washed thoroughly with brine, dried, and evaporated in vacuo to dryness to provide a mixture of the title product and benzhydryl 2-(3-phenoxyacetamido-2-oxoazetidin-1-yl)-2-methoxy-3-methyl-3-butenoate. The products were separated by preparative thin layer chromatography (silica gel plates developed with 1:1/hexane:ethylacetate). A purified sample of 46 mg of the title product was isolated: nmr (CDCl3) δ 2.20 (s, 3, CH3), 3.25 (s, 3, OCH3), 4.37 (s, 2, CH2OCH3), 3.73 (t, 1) and 3.50 (q, 1) [C4 --H], 4.97 (m, 1, C3 --H), 4.47 (s, 2, side chain CH2) and 7.2 (b, ArH).

Workup

  1. washThe resulting solution was washed thoroughly with brine
  2. customdried
  3. customevaporated in vacuo to dryness
  4. customto provide

Sources & evidence

ORD record
ord-f4d41fd3e56c45b887b4408a264b3d7d
Source dataset
uspto-grants-1980_03
Patent number
US04195021

Reaction notes

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