Carbon Disulfide → HCID 57296186, compound

HRID 1075221Notes

Reaction equation

HRID 1075221 reaction equation
[Na].[CH3:2][C@@H:3]([SH:19])[CH2:4][NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)=[O:7].[C:20](=[S:22])=[S:21].C(O[C@H:27]1[NH:30][C:29](=[O:31])[C@@H:28]1[C@H:32]([O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])[CH3:33])(=O)C>CO.C(OCC)(=O)C.C(O)(=O)C>[Si:35]([O:34][C@@H:32]([C@@H:28]1[C@@H:27]([S:21][C:20]([S:19][C@H:3]([CH3:2])[CH2:4][NH:5][C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[O:7])=[S:22])[NH:30][C:29]1=[O:31])[CH3:33])([C:38]([CH3:41])([CH3:39])[CH3:40])([CH3:37])[CH3:36]

Participants

8

Reactant 4

HCID 6348Carbon DisulfideHCID 5360545SodiumHCID 10935078AzetidonHCID 13175760(R)-1-methyl-2-(p-nitrobenzyloxycarbonylamino)ethanethiol

Product 1

HCID 57296186HCID 57296186, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of sodium (518 mg, 22.5 mmole) in methanol (100 ml) was added at -10° C. (R)-1-methyl-2-(p-nitrobenzyloxycarbonylamino)ethanethiol (6.61 g, 23.1 mmole). The mixture was stirred for 5 minutes, and then carbon disulphide (1.76 g, 23.1 mmole) was added and stirring was continued for a further 10 minutes. (3R, 4R)-4-acetoxy-3-[(R)-1-t-butyldimethylsilyloxyethyl]azetidin-2-one (6.46 g, 22.5 mmole) was then added at the same temperature, after which the bath temperature was raised to 0° C. over about 1 hour. About 300 mg of acetic acid was then added, and the reaction mixture was diluted with ethyl acetate and washed with a saturated aqueous solution of sodium chloride. After the solution had been dried, the solvent was distilled off under reduced pressure and the residue was purified through column chromatography (200 g of silica gel), eluted with a 10% v/v solution of ethyl acetate in benzene, affording the desired compound (10.8 g, 84%) in the form of a yellow oil.

Workup

  1. stirringstirring
  2. waitwas continued for a further 10 minutes
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. customAfter the solution had been dried
  5. distillationthe solvent was distilled off under reduced pressure
  6. customthe residue was purified through column chromatography (200 g of silica gel)
  7. washeluted with a 10% v/v solution of ethyl acetate in benzene

Sources & evidence

ORD record
ord-d3596550237146718beb8a84b64d4b78
Source dataset
uspto-grants-1983_07
Patent number
US04395418

Reaction notes

Loading…