Reaction #6389

ord-377f08373f404f4f90d97a6cafb8213b

Reaction equation

O=C1CC(C(=O)CCl)CO1
(RS)-4-Chloroacetyltetrahydrofuran-2-one
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC(C)(C)OC(=O)C(O)N1C(=O)[C@@H](NC(=O)COc2ccccc2)[C@H]1S
t-butyl (2RS)-2-hydroxy-[(3R,4R)-4-mercapto-3-phenoxyacetamidoazetidin-2-on-1-yl]acetate
→
CC(C)(C)OC(=O)C(O)N1C(=O)[C@@H](NC(=O)COc2ccccc2)[C@H]1SCC(=O)C1COC(=O)C1
title compound
Yield 68.0%
CC(C)(C)OC(=O)C(O)N1C(=O)[C@@H](NC(=O)COc2ccccc2)[C@H]1SCC(=O)C1COC(=O)C1
t-Butyl (2RS)-2-hydroxy-2-[(3R,4R)-4-[(4RS)-2-oxotetrahydrofuran-4-ylcarbonylmethylthio]-3-phenoxyacetamidoazetidin-2-on-1-yl]acetate
Yield 68.0%

Reactants

O=C1CC(C(=O)CCl)CO1
(RS)-4-Chloroacetyltetrahydrofuran-2-one
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CC(C)(C)OC(=O)C(O)N1C(=O)[C@@H](NC(=O)COc2ccccc2)[C@H]1S
t-butyl (2RS)-2-hydroxy-[(3R,4R)-4-mercapto-3-phenoxyacetamidoazetidin-2-on-1-yl]acetate

Reagents

None

Solvents

CC(C)=O
acetone
CCOC(C)=O
ethyl acetate

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Washwashed with water (x2) and brine
  2. 2
    Otherdried
  3. 3
    Concentrationconcentrated
  4. 4
    Otherflash chromatographed on silica gel eluting with 50,60,75,90% ethyl acetate in hexane

Procedure

(RS)-4-Chloroacetyltetrahydrofuran-2-one (2.060 g, 12.6 mmol), followed by potassium carbonate (0.690 g, 5 mmol) were added to crude t-butyl (2RS)-2-hydroxy-[(3R,4R)-4-mercapto-3-phenoxyacetamidoazetidin-2-on-1-yl]acetate (3.866 g) (prepared as described in Example 1c) in acetone (10 ml). The reaction was stirred 1 h. then diluted with ethyl acetate, washed with water (x2) and brine, dried, concentrated and flash chromatographed on silica gel eluting with 50,60,75,90% ethyl acetate in hexane to provide the title compound as a foam (3.458 g, 68%), νmax (CH2Cl2) 3380, 1780, 1680, 1235, 1150 cm-1 ; [Mass spectrum: +ve ion (thioglycerol) MH+ (509)].

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05246926uspto-grants-1993_09