Potassium Carbonate → HCID 54474289, compound

HRID 1450203Notes

Reaction equation

HRID 1450203 reaction equation
Cl[CH2:2][C:3]([CH:5]1[CH2:9][CH2:8][CH2:7][S: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][S: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 12519072HCID 12519072, compoundHCID 19975415HCID 19975415, compound

Product 1

HCID 54474289HCID 54474289, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

(RS)-2-Chloroacetyltetrahydrothiophene (2.50 g), (3R,4R)-4-mercapto-3-phenoxyacetamidoazetidin-2-one (4.60 g) and potassium carbonate (2.52 g) in DMF (30 ml) were stirred at room temperature for 2.5 h. T.l.c. analysis (ethyl acetate) showed completion of the reaction. The reaction mixture was diluted with ethyl acetate, washed with water (3×), brine and then dried. The solvent was evaporated and the residue flash chromatographed on silica gel eluting with 80% ethyl acetate/hexane to give the title compound as a pale yellow solid (4.194 g, 73%); m.p. 123° C., ethyl acetate/hexane; (Found: C, 53.51; H, 5.00; N, 7.39; S, 17.06%. C17H20N2O4S2 requires C, 53.66; H, 5.30; N, 7.36; S, 16.85%); νmax (CH2Cl2) 3405, 1785 and 1695 cm-1 ; δH (CDCl3), 1.81-1.95 (1H, m), 2.01-2.12 (2H, m), 2.28-2.42 (1H, m), 2.88 (2H, t, J 6.5 Hz), 3.39 and 3.56 with 3.39 and 3.45 (2H, 2 ABq, J 5.9 Hz), 4.07 and 4.09 (1H, 2 t, J 3.8 and 3.7 Hz), 4.58 (2H, s), 5.00 and 5.04 (1H, 2d, J 4.6 Hz), 5.58 and 5.60 (1H, 2 dd's,J 4.6, 9.2 Hz), 6.55 and 6.64 (1H, 2 br s), 6.94-7.07 (3H, m), 7.27-7.36 (2H, m), and 7.46 and 7.47 (1H, 2 br d, J 9.2 Hz).

Workup

  1. customcompletion of the reaction
  2. washwashed with water (3×), brine
  3. customdried
  4. customThe solvent was evaporated
  5. customthe residue flash chromatographed on silica gel eluting with 80% ethyl acetate/hexane

Sources & evidence

ORD record
ord-3f5aa190c09d449ea49f7283cbed6ed0
Source dataset
uspto-grants-1997_02
Patent number
US05602117

Reaction notes

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