Potassium Hydroxide → 1-(Methoxyethoxymethyl)-4-tritylthio-2-azetidinone

HRID 1680327Notes

Reaction equation

HRID 1680327 reaction equation
[OH-].[K+].[C:3]([S:22][CH:23]1[NH:26][C:25](=[O:27])[CH2:24]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:28][O:29][CH2:30][CH2:31][O:32][CH2:33]Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.ClCCl>[CH3:28][O:29][CH2:30][CH2:31][O:32][CH2:33][N:26]1[CH:23]([S:22][C:3]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:24][C:25]1=[O:27]

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 127801644-Tritylthio-2-azetidinone

Product 1

HCID 545286171-(Methoxyethoxymethyl)-4-tritylthio-2-azetidinoneYield 95.7%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a suspension of tetrabutylammonium bromide (322 mg, 1 mmole) and potassium hydroxide (85%, 70 mg,1.1 mmole) in dichloromethane (10 ml) cooled to 5° was added with vigorous stirring 4-tritylthio-2-azetidinone (345 mg, 1 mmole) and methoxyethoxymethyl chloride (187 mg, 1.5 mmole). The mixture was stirred at room temperature for 2 h, the solvent was evaporated and the residue partitioned between water and ethyl acetate. The dried organic phase was concentrated to leave a viscous oil (415 mg). Purification by column chromatography on silica gel eluting with ether (5%)-dichloromethane gave the title compound (206 mg, 48%) as an oil. δ (ppm, CDCl3): 7.30 (15H, m, aromatics), 4.57 (2H, AB quartet, N-CH2O), 4.46 (1H, dd, H-4), 3.50 (4H, s, OCH2CH2O), 3.30 (3H, s, CH3), 2.75 (2H, m, H-3).

Workup

  1. temperaturecooled to 5°
  2. additionwas added
  3. customthe solvent was evaporated
  4. customthe residue partitioned between water and ethyl acetate
  5. concentrationThe dried organic phase was concentrated

Sources & evidence

ORD record
ord-9102d3cbaa11472285841f24a051cc5c
Source dataset
uspto-grants-1981_06
Patent number
US04272437

Reaction notes

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