Potassium Carbonate → HCID 15102546, compound

HRID 582478Notes

Reaction equation

HRID 582478 reaction equation
[Si:1]([O:8][CH2:9][C@H:10]([O:13][CH:14]1[NH:17][C:16](=[O:18])[CH2:15]1)[CH2:11]I)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[Si:1]([O:8][CH2:9][C@@H:10]1[O:13][C@@H:14]2[N:17]([C:16](=[O:18])[CH2:15]2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Si:1]([O:8][CH2:9][C@@H:10]1[O:13][C@H:14]2[N:17]([C:16](=[O:18])[CH2:15]2)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 67649817HCID 67649817, compound

Product 2

HCID 15102545HCID 15102545, compoundYield 28%HCID 15102546HCID 15102546, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-[(S)-1-(tert-butyldimethylsilyl) oxymethyl-2-iodoethoxy]-azetidin-2-one which was prepared by the known method (6.8 g, 17.7 mmole), and powdered K2CO3 (6.1 g, 44 mmole) in DMSO (100 ml) was stirred at room temperature overnight and then diluted with ethyl acetate, washed with water, brine, and dried over sodium sulfate. After removal of solvent, the residue was purified by repeated silica gel column chromatography using hexane-ethyl acetate (9:1) as eluent. The title compounds (3R, 5S)-3-(tert-butyldimethyl silyl)oxymethyl-4-oxa-1-azabicyclo [3,2,0] heptan-7-one (Ref. 1A) (1.85 g, yield 41%) and its isomer (3R, 5R)-3-(tert-butyldimethyl silyl)oxymethyl-4-oxa-1-azabicyclo [3,2,0] heptan-7-one (Ref. 1B) (1.28 g, yield 28%) were obtained as oil.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulfate
  3. customAfter removal of solvent
  4. customthe residue was purified

Sources & evidence

ORD record
ord-be7d7d8a973a44a196c4a17644dc6b91
Source dataset
uspto-grants-1999_07
Patent number
US05925633

Reaction notes

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