Ethyl Acetate → 4-Methoxybenzyl (2RS)-2-hydroxy-2-[(3R,4R)-3-phenylacetamido-4-(tetrahydropyran-4-ylcarbonylmethylthio)azetidin-2-on-1-yl]acetate

HRID 376617Notes

Reaction equation

HRID 376617 reaction equation
[OH:1][CH:2]([N:15]1[C:21](=[O:22])[C@@H:20]2[C@H:16]1[S:17][C:18]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[N:19]2)[C:3]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)=[O:4].Br[CH2:31][C:32]([CH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1)=[O:33].C(=O)([O-])[O-:41].[K+].[K+].C(OCC)(=O)C>CC(C)=O>[OH:1][CH:2]([N:15]1[C@H:16]([S:17][CH2:31][C:32]([CH:34]2[CH2:39][CH2:38][O:37][CH2:36][CH2:35]2)=[O:33])[C@H:20]([NH:19][C:18](=[O:41])[CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:21]1=[O:22])[C:3]([O:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1)=[O:4]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 131972252-Bromo-1-(oxan-4-yl)ethan-1-oneHCID 536561234-Methoxybenzyl (RS)-2-hydroxy-2-[(lR,5R)-3-benzyl-4-thia-2,6-diazabicyclo[3.2.0)hept-2-en-7-on-6-yl]acetate

Product 1

HCID 540298234-Methoxybenzyl (2RS)-2-hydroxy-2-[(3R,4R)-3-phenylacetamido-4-(tetrahydropyran-4-ylcarbonylmethylthio)azetidin-2-on-1-yl]acetateYield 76%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Crude 4-methoxybenzyl (2RS)-2-hydroxy-2-[(3R,4R)-4-mercapto-3-phenylacetamidoazetidin-2-on-1-yl acetate {prepared from 4-methoxybenzyl (2RS)-2-hydroxy-2-[(1R,5R)-3-benzyl-4-thia-2,6-diazabicyclo[3.2.0]hept-2-en-7-on-6-yl]acetate (8.35g, 20mmol)} was dissolved in acetone (25ml) and treated with a solution of 4-bromoacetyltetrahydropyran (G. H. Harnest and A. Burger, J. Amer. Chem. Soc., 1943, 65, 370) (4.4g, 20mmol). After 20min., potassium carbonate (1.38g, 10mmol) was added and the mixture stirred again for a further 45min. Excess ethyl acetate was then added and the organic solution washed with water, brine and dried over anhydrous MgSO4. Evaporation of solvent and chromatography of the residue on silica gel using 50% hexane in ethyl acetate to 100% ethyl acetate gave the title compound as a pale yellow foam (8.5g; 76%); vmax (CHCl3) 3420, 1780, 1750, 1680 and 1615cm-1. [Mass spectrum: +ve ion (3-nitrobenzyl alcohol, sodium acetate) MNa+ (579)].

Workup

  1. washthe organic solution washed with water, brine
  2. dry with materialdried over anhydrous MgSO4
  3. customEvaporation of solvent and chromatography of the residue on silica gel using 50% hexane in ethyl acetate to 100% ethyl acetate

Sources & evidence

ORD record
ord-6039d91f03ef4bb59be5d95cdeefaa4d
Source dataset
uspto-grants-2000_02
Patent number
US06020329

Reaction notes

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