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

HRID 1900188Notes

Reaction equation

HRID 1900188 reaction equation
CN1CCOCC1.Cl[C:9]([O:11][CH:12]([CH3:16])[CH2:13][O:14][CH3:15])=[O:10].[C:17]([C:19]1[CH:36]=[CH:35][C:22]([O:23][CH2:24][CH:25]([NH:27][C:28](=[O:34])[C@H:29]([CH:31]([CH3:33])[CH3:32])[NH2:30])[CH3:26])=[CH:21][CH:20]=1)#[N:18].O>C(Cl)Cl>[C:17]([C:19]1[CH:20]=[CH:21][C:22]([O:23][CH2:24][CH:25]([NH:27][C:28](=[O:34])[C@H:29]([CH:31]([CH3:32])[CH3:33])[NH:30][C:9]([O:11][CH:12]([CH3:16])[CH2:13][O:14][CH3:15])=[O:10])[CH3:26])=[CH:35][CH:36]=1)#[N:18]

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 133055461-Methoxypropan-2-yl chloroformateHCID 22866848N1-[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide

Product 1

HCID 54269444N1-[2-(4-cyanophenoxy)-1-methylethyl]-N2-(2-methoxy-1-methylethyl)oxycarbonyl-L-valinamideYield 20.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.0 g of N-methylmorpholine, and subsequently 0.7 g of 2-methoxy-1-methylethyl chloroformate were added to a suspension containing 1.5 g of N1 -[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide suspended in 150 ml of methylene chloride at -20° C. The mixture was allowed to sit and warm naturally to room temperature and stirred for 2 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 then the methylene chloride was removed under reduced pressure. The residue was purified by column chromatography on silica gel, thus obtaining 0.37 g of the desired product in the form of a white plated crystal (yield: 20%).

Workup

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

Sources & evidence

ORD record
ord-bd4729f38c534aeba134aa0e7d0a5076
Source dataset
uspto-grants-1996_11
Patent number
US05574064

Reaction notes

Loading…