N-Methylpiperidine → HCID 22941573, compound

HRID 343646Notes

Reaction equation

HRID 343646 reaction equation
CN1CCCCC1.[CH3:8][NH:9][O:10][CH3:11].[CH3:12][N:13]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[C@H:14]([C:36]([OH:38])=O)[CH2:15][S:16][C:17]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.ClC(OCC(C)C)=O>ClCCl>[CH3:12][N:13]([C:39]([O:41][C:42]([CH3:45])([CH3:43])[CH3:44])=[O:40])[C@@H:14]([CH2:15][S:16][C:17]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:36]([N:9]([O:10][CH3:11])[CH3:8])=[O:38]

Participants

6

Reactant 4

HCID 12291N-Methylpiperidine2×HCID 14232N,O-DimethylhydroxylamineHCID 62365Isobutyl chloroformateHCID 53939267HCID 53939267, compound

Product 1

HCID 22941573HCID 22941573, compoundYield 49.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
20 °C

Procedure

1.96 cm3 of N-methylpiperidine are added, at a temperature in the region of 0° C., to a suspension of 1.57 g of N,O-dimethylhydroxylamine in 10 cm3 of dichloromethane. This solution is added to the reaction mixture containing 7.8 g of N-methyl-N-tert-butoxycarbonyl-S-triphenylmethyl-L-cysteine, 1.96 cm3 of N-methylpiperidine and 2.08 cm3 of isobutyl chloroformate in 20 cm3 of dichloromethane at a temperature in the region of -8° C. The reaction mixture is stirred for 2 hours at a temperature in the region of 20° C. and then washed with a 10% (w/v) aqueous citric acid solution, then with a 2% (w/v) aqueous sodium hydroxide solution and finally with a saturated sodium chloride solution. The organic phase is dried over magnesium sulphate, filtered and concentrated under reduced pressure. The thick red oil obtained is purified by chromatography on silica [eluent: dichloromethane/ethyl acetate (95/5 by volume)]. 4.2 g of N-(N-methyl-2(R)-tert-butoxycarbonylamino-3-(triphenylmethylthio)propionyl)-N,O-dimethylhydroxyl-amine are obtained in the form of a red oil, the characteristics of which are the following:

Workup

  1. additionThis solution is added to the reaction mixture
  2. washwashed with a 10% (w/v) aqueous citric acid solution
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe thick red oil obtained
  7. customis purified by chromatography on silica [eluent: dichloromethane/ethyl acetate (95/5 by volume)]

Sources & evidence

ORD record
ord-c13542d08767473290a48fd953b6a180
Source dataset
uspto-grants-1999_01
Patent number
US05861529

Reaction notes

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