Carbon Disulfide → HCID 88361362, compound

HRID 128502Notes

Reaction equation

HRID 128502 reaction equation
[C:1](=[S:3])=[S:2].Br[CH2:5][CH2:6]Br.[H-].[Na+].[CH2:10]([O:12][C:13]([CH2:15][C:16]([NH:18][C@@H:19]1[C:33](=[O:34])[N:21]2[CH:22]([C:27]([O:29][CH2:30][CH:31]=[CH2:32])=[O:28])[C:23]([CH3:26])([CH3:25])[S:24][C@H:20]12)=[O:17])=[O:14])[CH3:11]>CN(C)C=O.C1(C)C=CC=CC=1>[S:2]1[CH2:6][CH2:5][S:3][C:1]1=[C:15]([C:13]([O:12][CH2:10][CH3:11])=[O:14])[C:16]([NH:18][C@@H:19]1[C:33](=[O:34])[N:21]2[CH:22]([C:27]([O:29][CH2:30][CH:31]=[CH2:32])=[O:28])[C:23]([CH3:26])([CH3:25])[S:24][C@H:20]12)=[O:17]

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 67785066HCID 67785066, compound

Product 1

HCID 88361362HCID 88361362, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Carbon disulfide (1.5 mL), 1,2-dibromoethane (845 mg, 4.5 mmol) and sodium hydride, 60% (240 mg, 6 mmol) were added sequentially to a solution of allyl 6β-[(ethoxycarbonyl)acetamido]-2,2-dimethylpenam-3-carboxylate (1.11 g, 3 mmol) in 3 mL of dimethylformamide at 0° C. The reaction mixture was stirred at 0° C. for 30 min under a nitrogen atmosphere. The mixture was diluted with toluene, washed with water and saturated NaCl solution, and dried over Na2SO4. After concentration, the residue was chromatographed on silica gel with chloroform-ethyl acetate (95:5) as the eluant to give the title compound (926 mg, 65%) as yellow crystals: m.p. 116°-117° C. (ethyl acetate); IR (CHCl3) 1790, 1750, 1680 cm-1; 1 H NMR (CDCl3) δ 1.39 (3H, t, J=7Hz, CH2CH3), 1.49 and 1.66 (each 3H, s, C2 -(CH3)2), 3.32 (4H, s, SCH2CH2S), 4.30-4.40 (2H, m, CH2CH3), 4.46 (1H, s, C3 -H), 4.62-4.68 (2H, m, OCH2CH=CH2), 5.26-5.40 (2H, m OCH2CH=CH2), 5.57 (1H, d, J=4Hz, C5 -H), 5.83 (1H, dd, J=4 and 9Hz, C6 -H), 5.83-6.00 (1H, m, OCH2CH=CH2), 9.05 (1H, d, J=9Hz, NH).

Workup

  1. washwashed with water and saturated NaCl solution
  2. dry with materialdried over Na2SO4
  3. concentrationAfter concentration
  4. customthe residue was chromatographed on silica gel with chloroform-ethyl acetate (95:5) as the eluant

Sources & evidence

ORD record
ord-9db223bd2523403d981ad3b91ab3dede
Source dataset
uspto-grants-1995_11
Patent number
US05464616

Reaction notes

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