Water → N1-[2-(4-cyanophenoxy)-1-methylethyl)-N2-(3-tetrahydrofuranyl)oxycarbonyl-L-valinamide

HRID 1900185Notes

Reaction equation

HRID 1900185 reaction equation
CN1CCOCC1.Cl[C:9]([O:11][CH:12]1[CH2:16][CH2:15][O:14][CH2:13]1)=[O:10].Cl.[C:18]([C:20]1[CH:37]=[CH:36][C:23]([O:24][CH2:25][CH:26]([NH:28][C:29](=[O:35])[C@H:30]([CH:32]([CH3:34])[CH3:33])[NH2:31])[CH3:27])=[CH:22][CH:21]=1)#[N:19].O>C(Cl)Cl>[C:18]([C:20]1[CH:21]=[CH:22][C:23]([O:24][CH2:25][CH:26]([NH:28][C:29](=[O:35])[C@H:30]([CH:32]([CH3:33])[CH3:34])[NH:31][C:9]([O:11][CH:12]2[CH2:16][CH2:15][O:14][CH2:13]2)=[O:10])[CH3:27])=[CH:36][CH:37]=1)#[N:19]

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 15291007Oxolan-3-yl chloroformateHCID 22866849N1-[2-(4-cyanophenoxy)-1-methylethyl]L-valinamide hydrochloride

Product 1

HCID 86749989N1-[2-(4-cyanophenoxy)-1-methylethyl)-N2-(3-tetrahydrofuranyl)oxycarbonyl-L-valinamideYield 60.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.0 g of N-methylmorpholine, and subsequently 0.7 g of 3-tetrahydrofuranyl chloroformate were added to a suspension containing 1.5 g of N1 -[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide hydrochloride suspended in 100 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 dichloromethane 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 1.1 g of the desired product in the form of white powder (yield: 61%).

Workup

  1. washAfter the dichloromethane 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-4544edfb754f4158a47e51118dc53b11
Source dataset
uspto-grants-1996_11
Patent number
US05574064

Reaction notes

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