HCID 12416141, compound → HCID 54027933, compound

HRID 1701667Notes

Reaction equation

HRID 1701667 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH2:15][N:14]([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:13]1=[O:36])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(Cl)Cl.C(N(CC)CC)C>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH2:15][N:14]([C:16](=[C:33]([CH3:34])[CH3:35])[C:17]([O:19][CH:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:18])[C:13]1=[O:36])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 12416141HCID 12416141, compound

Product 1

HCID 54027933HCID 54027933, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 50 mg of benzhydryl 2-(3-phenoxyacetamido-2-oxoazetidin-1-yl)-3-methyl-3-butenoate in 10 ml of methylene chloride was added 3 drops of triethylamine. After 2 hours at room temperature the reaction mixture was washed thoroughly with brine and dilute acid. After drying, the solution was evaporated in vacuo to dryness to provide 50 mg of the title product: nmr (CDCl3) δ 2.05 (s, 3, CH3), 2.25 (s, 3, CH3), 3.60 (2, m, azetidinone C4 --H), 5.02 (m, 1, C3 --H), 4.55 (s, 2, --OCH2CO--), and 7.2 (b, 15, ArH).

Workup

  1. washAfter 2 hours at room temperature the reaction mixture was washed thoroughly with brine
  2. additiondilute acid
  3. customAfter drying
  4. customthe solution was evaporated in vacuo to dryness

Sources & evidence

ORD record
ord-064fefd62ad943f3b53957f6ae862594
Source dataset
uspto-grants-1980_03
Patent number
US04195021

Reaction notes

Loading…