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Water → N1-[2-(4-cyanophenoxy)-1-methylethyl]-N2-(3,4-dimethylphenoxycarbonyl)-L-valinamide

HRID 1900191
Notes
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Reaction equation

HRID 1900191 reaction equation
CN1CCOCC1.Cl[C:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=1)=[O:10].[C:20]([C:22]1[CH:39]=[CH:38][C:25]([O:26][CH2:27][CH:28]([NH:30][C:31](=[O:37])[C@H:32]([CH:34]([CH3:36])[CH3:35])[NH2:33])[CH3:29])=[CH:24][CH:23]=1)#[N:21].O>C(Cl)Cl>[C:20]([C:22]1[CH:23]=[CH:24][C:25]([O:26][CH2:27][CH:28]([NH:30][C:31](=[O:37])[C@H:32]([CH:34]([CH3:35])[CH3:36])[NH:33][C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[C:14]([CH3:19])[CH:13]=2)=[O:10])[CH3:29])=[CH:38][CH:39]=1)#[N:21]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 220262003,4-Xylyl chloroformateHCID 22866848N1-[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide

Product 1

HCID 54096664N1-[2-(4-cyanophenoxy)-1-methylethyl]-N2-(3,4-dimethylphenoxycarbonyl)-L-valinamideYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.6 g of N-methylmorpholine, and subsequently 1.2 g of 3,4-dimethylphenyl chloroformate were added to a suspension containing 1.5 g of N1 -[2-(4-cyanophenoxy)-1-methylethyl]-L-valinamide suspended in 50 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 under reduced pressure. The residue was purified by column chromatography on silica gel, thus obtaining 1.7 g of the desired product in the form of a white crystal (yield: 74%).

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-baf761d4981a472183262f17aae57fd6
Source dataset
uspto-grants-1996_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05574064

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes