Water → HCID 54069852, compound

HRID 1900198Notes

Reaction equation

HRID 1900198 reaction equation
CN1CCOCC1.Cl[C:9]([O:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10].[C:18]([C:20]1[CH:38]=[CH:37][C:23]([O:24][CH2:25][CH:26]([NH:28][C:29](=[O:36])[C@H:30]([CH2:32][CH:33]([CH3:35])[CH3:34])[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:36])[C@H:30]([CH2:32][CH:33]([CH3:34])[CH3:35])[NH:31][C:9]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:10])[CH3:27])=[CH:37][CH:38]=1)#[N:19]

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 15891Phenyl chloroformateHCID 22866845HCID 22866845, compound

Product 1

HCID 54069852HCID 54069852, compoundYield 71.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.5 g of N-methylmorpholine, and subsequently 0.8 g of phenyl chloroformate were added to a suspension containing 1.5 g of N1 -[2-(4-cyanophenoxy)-1-methylethyl]-L-leucinamide suspended in 40 ml of methylene chloride at -15° C. The mixture was allowed to sit and warm naturally to room temperature and 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 then the methylene chloride was removed tinder reduced pressure. The residue was purified by column chromatography on silica gel, thus obtaining 1.5 g of the desired product in the form of colorless powder (yield: 73%)

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 tinder reduced pressure
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0871a196346343ddbb0e75b71d6745cb
Source dataset
uspto-grants-1996_11
Patent number
US05574064

Reaction notes

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