Ethyl Acetate → HCID 53787898, compound

HRID 1701677Notes

Reaction equation

HRID 1701677 reaction equation
[OH-].[Na+].[O:3]([CH2:10][C:11]([NH:13][CH:14]1[CH2:17][N:16]([C:18](=[C:35]([CH3:40])[CH2:36][O:37]C=O)[C:19]([O:21][CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[C:15]1=[O:41])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C(OCC)(=O)C>C1COCC1>[O:3]([CH2:10][C:11]([NH:13][CH:14]1[CH2:17][N:16]([C:18](=[C:35]([CH3:40])[CH2:36][OH:37])[C:19]([O:21][CH:22]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])[C:15]1=[O:41])=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 53878604HCID 53878604, compound

Product 1

HCID 53787898HCID 53787898, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6 ml of 0.1 N aqueous sodium hydroxide at 0° was added a solution of 338 mg (0.6 mmol) of benzhydryl 2-(3-phenoxyacetamido-2-oxoazetidin-1-yl)-3-methyl-4-formyloxy-2-butenoate in 10 ml of cold THF. After 30 minutes, ethyl acetate was added. The organic layer was separated, washed with dilute acid and brine, dried, and evaporated in vacuo to dryness to provide 250 mg of a multi-component mixture. Separation by preparative thin layer chromatography (silica gel plates developed with 3:1/ethyl acetate:hexane) provided 35 mg of the title product: nmr (CDCl3) δ 2.28 (s, 3, CH3), 4.72 (s, 2, --CH2OH), 3.60 (m, 2, C4 --H), 5.02 (m, 1, C3 --H), 4.55 (s, 2, side chain CH2), and 7.2 (b, ArH).

Workup

  1. customThe organic layer was separated
  2. washwashed
  3. additionwith dilute acid and brine
  4. customdried
  5. customevaporated in vacuo to dryness

Sources & evidence

ORD record
ord-224a55c12c7240afbca5c6550e19771c
Source dataset
uspto-grants-1980_03
Patent number
US04195021

Reaction notes

Loading…