Potassium Carbonate → HCID 54526078, compound

HRID 1421783Notes

Reaction equation

HRID 1421783 reaction equation
Cl[CH2:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][O:6]1)=[O:4].[SH:10][C@H:11]1[NH:14][C:13](=[O:15])[C@H:12]1[NH:16][C:17](=[O:26])[CH2:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[O:19]([CH2:18][C:17]([NH:16][C@H:12]1[C@@H:11]([S:10][CH2:2][C:3]([CH:5]2[CH2:9][CH2:8][CH2:7][O:6]2)=[O:4])[NH:14][C:13]1=[O:15])=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10396974Ethanone, 2-chloro-1-(tetrahydro-2-furanyl)- (9CI)HCID 12519072HCID 12519072, compound

Product 1

HCID 54526078HCID 54526078, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(RS)-2-Chloroacetyltetrahydrofuran (2.46 g, 16.5 mmol), (3R,4R)-4-mercapto-3-phenoxyacetamidoazetidin-2-one (4.157 g, 16.5 mmol) and potassium carbonate (2.227 g, 16.5 mmol) in DMF (10 ml) were stirred for 2 h, diluted with ethyl acetate, washed twice with water and with brine, dried concentrated and flash chromatographed eluting with 40,30,20,10 and 0% hexane in ethyl acetate to give the title compound as a foam (3.547 g, 59%); νmax (CH2Cl2) 3405, 1785, 1693, 1520, 1496 and 1240 cm-1 ; δ(CDCl3, 250 MHz) 1.9-2.3 (4H, m), 3.42 and 3.62, 3.46 and 3.56 (together 2H, 2 ABq, J15.8 Hz, 15.4 Hz), 3.85-4.0 (2H, m), 4.4-4.5 (1H, m), 4.58 (2H, s), 5.01, 5.04 (together 1H, 2d, J4.7 Hz), 5.59 (1H, dd, J 8.8, 4.5 Hz) 6.62, 6.68 (together 1H, 2s), 6.9-7.4 (5H, m) and 7.45, 7.47 (together 1H, 2d, J8.8 Hz). [Mass spectrum: M+ (364)].

Workup

  1. washwashed twice with water and with brine
  2. customdried
  3. concentrationconcentrated
  4. customflash chromatographed
  5. washeluting with 40,30,20,10 and 0% hexane in ethyl acetate

Sources & evidence

ORD record
ord-a630e8adbf02476681d673a21f8e3d9c
Source dataset
uspto-grants-2000_06
Patent number
US06077952

Reaction notes

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