Carbon Disulfide → HCID 13730272, compound

HRID 65205Notes

Reaction equation

HRID 65205 reaction equation
C([S:4][CH:5]([CH2:21][NH:22][C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:24])[CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1)=[O:9])(=O)C.C[O-].[Na+].[C:39](=[S:41])=[S:40].C(O[CH:46]1[NH:49][C:48](=[O:50])[CH:47]1[C@H:51]([O:53][Si:54]([C:57]([CH3:60])([CH3:59])[CH3:58])([CH3:56])[CH3:55])[CH3:52])(=O)C>CO.O1CCCC1.O.C(O)(=O)C>[Si:54]([O:53][C@@H:51]([C@@H:47]1[C@@H:46]([S:40][C:39]([S:4][CH:5]([CH2:6][NH:7][C:8]([O:10][CH2:11][C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)=[O:9])[CH2:21][NH:22][C:23]([O:25][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=2)=[O:24])=[S:41])[NH:49][C:48]1=[O:50])[CH3:52])([C:57]([CH3:60])([CH3:58])[CH3:59])([CH3:56])[CH3:55]

Participants

9

Reactant 4

HCID 6348Carbon DisulfideHCID 10942334Sodium Methoxide2×HCID 130738914-acetoxy-3-[1-(R)-t-butyldimethylsilyloxyethyl)-2-azetidinoneHCID 137302702-Acetylthio-1,3-bis(p-nitrobenzyloxycarbonylamino)propane

Product 1

HCID 13730272HCID 13730272, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

5.3 g of 2-acetylthio-1,3-bis(p-nitrobenzyloxycarbonylamino)propane in a mixture of 161 ml of methanol and 40 ml of tetrahydrofuran were cooled to -20° C. To the solution were added 9.95 ml of a methanolic solution of sodium methoxide containing 1 mM of sodium methoxide per 1 ml of methanol. The mixture was stirred at -10° to -15° C. for 30 minutes, after which it was mixed with 0.961 ml of carbon disulphide and stirred at -20° C. for 15 minutes. Then 20 ml of a methanolic solution containing 3.59 g of 4-acetoxy-3-[1-(R)-t-butyldimethylsilyloxyethyl)-2-azetidinone was added to the above mixture and stirred at -20° C. for 1 hour. The mixture was cooled to -50° C. and then poured into a mixture of 20 ml of acetic acid and 200 ml of water. The mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulphate. The solvent was distilled off and the residue was subjected to medium pressure column chromatography througn silica gel, eluted with 3:1-2:1 by volume mixtures of benzene and ethyl acetate, to give 6.1 g of the desired compound.

Workup

  1. stirringstirred at -20° C. for 15 minutes
  2. additionwas added to the above mixture
  3. stirringstirred at -20° C. for 1 hour
  4. temperatureThe mixture was cooled to -50° C.
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe extract was washed with a saturated aqueous solution of sodium chloride
  7. dry with materialdried over anhydrous sodium sulphate
  8. distillationThe solvent was distilled off
  9. washeluted with 3:1-2:1 by volume mixtures of benzene and ethyl acetate

Sources & evidence

ORD record
ord-fd153148a334471a80be5c976744feec
Source dataset
uspto-grants-1986_09
Patent number
US04613595

Reaction notes

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