Dimethyl Sulfide → HCID 86739391, compound

HRID 543500Notes

Reaction equation

HRID 543500 reaction equation
[F:1][CH2:2][CH:3]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:4][C:5](=C)[CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].[O:24]=[O+][O-].CSC>CO.C(Cl)Cl>[F:1][CH2:2][CH:3]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:4][C:5](=[O:24])[CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]

Participants

6

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 13109089HCID 13109089, compound

Product 1

HCID 86739391HCID 86739391, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

1-Fluoro-2,5-di-t-butoxycarbonylamino-4-methylenepentane (800 mg, 2.4 mmoles) prepared as in Example 1, Step F, dissolved in a 1/1 mixture (30 mL) of methanol and methylene chloride is cooled to -78° C. and treated with ozone (flow rate 0.3 L/min) for 6 min and 15 sec. An excess of dimethylsulfide is added (about 2 mL) and then the reaction mixture is allowed to warm up to room temperature. After concentration, the residue is extracted twice with methylene chloride/water and work-up of the organic layer affords 800 mg of an oil which is crystallized from ether/petroleum ether (410 mg, 51%).

Workup

  1. temperatureto warm up to room temperature
  2. concentrationAfter concentration
  3. extractionthe residue is extracted twice with methylene chloride/water

Sources & evidence

ORD record
ord-966b9adb6fb8471dad2f4a43aa593116
Source dataset
uspto-grants-1984_05
Patent number
US04446151

Reaction notes

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