Carbon Disulfide → HCID 15297251, compound

HRID 128500Notes

Reaction equation

HRID 128500 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:11]2[CH:12]([C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[C:13]([CH3:16])([CH3:15])[S:14][C@H:10]12)=[O:7])=[O:4].[C:25](=[S:27])=[S:26].[H-].[Na+].Br[CH:31](Br)[CH3:32]>CN(C)C=O.C1(C)C=CC=CC=1>[S:26]1[CH2:32][CH2:31][S:27][C:25]1=[C:5]([C:3]([O:2][CH3:1])=[O:4])[C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:11]2[CH:12]([C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])[C:13]([CH3:16])([CH3:15])[S:14][C@H:10]12)=[O:7]

Participants

7

Reactant 4

HCID 6348Carbon DisulfideHCID 112011,1-DibromoethaneHCID 24758Sodium hydrideHCID 15297250HCID 15297250, compound

Product 1

HCID 15297251HCID 15297251, compoundYield 88%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of allyl 6β-[(methoxycarbonyl)acetamido]-2,2-dimethylpenam-3-carboxylate (713 mg, 2 mmol) in 2 mL of sieve-dried dimethylformamide at 0° C. was added carbon disulfide (1 mL), then sodium hydride, 60% (160 mg, 4 mmol), portionwise. The reaction mixture was stirred at 0° C. for 10 min under a nitrogen atmosphere, and treated with dibromoethane (413 mg, 2.2 mmol). The mixture was stirred at 0° C. for 30 min, diluted with toluene, washed with water and saturated NaCl solution, and dried over Na2SO4. The solution was concentrated to give a brown oil, which was chromatographed on silica gel eluting with chloroform-ethyl acetate (95:5) to yield the title compound (811 mg, 88%) as a yellow foam: IR (CHCl3) 1790, 1750, 1685 cm-1; 1 H NMR (CDCl3) δ 1.50 and 1.67 (each 3H, s, C2-(CH 3)2), 3.33 (4H, s, SCH2CH2S), 3.88 (3H, s, CO2CH3), 4.48 (1H, s, C3 -H), 4.64-4.68 (2H, m, OCH2CH=CH2), 5.25-5.42 (2H, m, OCH2CH=CH2), 5.58 (1H, d, J=4Hz, C5 -H), 5.83 (1H, dd, J=4 and 9Hz, C6 -H), 5.85-6.00 (1H, m, OCH2CH=CH2), 8.97 (1H, d, J=9Hz, NH).

Workup

  1. stirringThe mixture was stirred at 0° C. for 30 min
  2. washwashed with water and saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. concentrationThe solution was concentrated
  5. customto give a brown oil, which
  6. customwas chromatographed on silica gel eluting with chloroform-ethyl acetate (95:5)

Sources & evidence

ORD record
ord-1ea83ee0f39c41ab90db25e347c01eb2
Source dataset
uspto-grants-1995_11
Patent number
US05464616

Reaction notes

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