Water → N1-[2-(4-cyanophenoxy)-1-methylethyl]-N2-(phenylthio)thiocarbonyl-L-valinamide

HRID 1900178

Reaction equation

HRID 1900178 reaction equation
CN1CCOCC1.[C:8]([C:10]1[CH:27]=[CH:26][C:13]([O:14][CH2:15][CH:16]([NH:18][C:19](=[O:25])[C@H:20]([CH:22]([CH3:24])[CH3:23])[NH2:21])[CH3:17])=[CH:12][CH:11]=1)#[N:9].Cl[C:29]([S:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[S:30].O>C(Cl)Cl>[C:8]([C:10]1[CH:11]=[CH:12][C:13]([O:14][CH2:15][CH:16]([NH:18][C:19](=[O:25])[C@H:20]([CH:22]([CH3:23])[CH3:24])[NH:21][C:29]([S:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[S:30])[CH3:17])=[CH:26][CH:27]=1)#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 592675Phenyl ChlorodithioformateHCID 22866848N1-[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide

Product 1

HCID 53873873N1-[2-(4-cyanophenoxy)-1-methylethyl]-N2-(phenylthio)thiocarbonyl-L-valinamideYield 68.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.5 g of N-methylmorpholine was added to a suspension containing 1.4 g of N1 -[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide suspended in 40 ml of methylene chloride, at -15° C. After 0.9 g of phenyl chlorodithioformate was added to the mixture at -15° C., the reaction mixture was allowed to sit and, warm naturally to room temperature while being stirred, and was stirred for 15 hours at room temperature. Water was subsequently added to the reaction mixture. After the methylene chloride layer was washed with water, the organic layer was dried over anhydrous magnesium sulfate and the methylene chloride was removed under reduced pressure. The residue was purified by column chromatography on silica gel, thus obtaining 1.4 g of the desired product in the form of a yellow glutinous substance (yield: 66%).

Workup

  1. stirringwas stirred for 15 hours at room temperature
  2. washAfter the methylene chloride layer was washed with water
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customthe methylene chloride was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-379fa347b45b4d9b9dd21b027bd28161
Source dataset
uspto-grants-1996_11
Patent number
US05574064

Linked notes

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