Potassium Carbonate → HCID 53804210, compound

HRID 6293Notes

Reaction equation

HRID 6293 reaction equation
Cl[CH2:2][C:3]([CH:5]1[CH2:9][O:8][C:7](=[O:10])[CH2:6]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].[OH:17][CH:18]([N:26]1[C@H:29]([SH:30])[C@H:28]([NH:31][C:32](=[O:41])[CH2:33][O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:27]1=[O:42])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>CC(C)=O.C(OCC)(=O)C>[OH:17][CH:18]([N:26]1[C@H:29]([S:30][CH2:2][C:3]([CH:5]2[CH2:9][O:8][C:7](=[O:10])[CH2:6]2)=[O:4])[C@H:28]([NH:31][C:32](=[O:41])[CH2:33][O:34][C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:27]1=[O:42])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 197941584-(2-Chloroacetyl)oxolan-2-oneHCID 54462128t-butyl (2RS)-2-hydroxy-[(3R,4R)-4-mercapto-3-phenoxyacetamidoazetidin-2-on-1-yl]acetate

Product 1

HCID 53804210HCID 53804210, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

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)].

Workup

  1. washwashed with water (x2) and brine
  2. customdried
  3. concentrationconcentrated
  4. customflash chromatographed on silica gel eluting with 50,60,75,90% ethyl acetate in hexane

Sources & evidence

ORD record
ord-377f08373f404f4f90d97a6cafb8213b
Source dataset
uspto-grants-1993_09
Patent number
US05246926

Reaction notes

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