4-Methoxybenzyl alcohol → HCID 22876570, compound

HRID 861893Notes

Reaction equation

HRID 861893 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1.CC1(C)[O:17][C:16](=O)[CH:15]=[C:14]([CH2:19][CH2:20][C@H:21]2[NH:24][C:23](=[O:25])[C@H:22]2[NH:26][C:27](=[O:35])[CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:13]1>C1(C)C=CC=CC=1>[O:13]=[C:14]([CH2:19][CH2:20][C@H:21]1[NH:24][C:23](=[O:25])[C@H:22]1[NH:26][C:27](=[O:35])[CH2:28][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:15][C:16]([O:8][CH2:7][C:6]1[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:17]

Participants

4

Reactant 2

HCID 77384-Methoxybenzyl alcoholHCID 22876565HCID 22876565, compound

Product 1

HCID 22876570HCID 22876570, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 4-methoxybenzyl alcohol (1.50 g, 10.87 mmol) in toluene (6 ml) was added to a solution of (3S,4R)-4-[(2,2-dimethyl-4H-1,3-dioxin-4-on-6-yl)ethyl]-3-phenylacetamidoazetidin-2-one (3.86 g, 10.78 mmol) and heated to reflux for 1.5 h. The reaction mixture was concentrated in vacuo and the residue triturated with toluene to give the title compound (3.50 g, 75%) as a crude product; νmax (CH2Cl2) 3412, 1772, 1747, 1717, 1684 and 1514 cm-1 ; δH (CDCl3) 1.63 (2H, m), 2.39 (2H, t, J7.0 Hz), 3.37 (2H, s), 3.58 (2H, s), 3.68 (1H, m), 3.81 (3H, s), 5.09 (2H, s), 5.18 (1H, m), 6.26 (1H, br.s, exch.), 6.63 (1H, d, J 7.9 Hz), 6.89 (2H, d, J 8.6 Hz) and 7.21-7.38 (7H, m); m/z (FAB, -ve ion, thioglycerol) 437 (M-H)-.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1.5 h
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customthe residue triturated with toluene

Sources & evidence

ORD record
ord-39adc2c0c5c74717a36c59214ff0f9b9
Source dataset
uspto-grants-1998_02
Patent number
US05716948

Reaction notes

Loading…