Water → HCID 67638942, compound
Reaction equation
CN1CCOCC1.Cl[C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10].[NH2:15][CH:16]1[CH2:20][CH2:19][CH2:18][CH:17]1[CH2:21][C:22]([NH:24][CH:25]([CH3:36])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]#[N:35])=[CH:30][CH:29]=1)=[O:23].O>C(Cl)Cl>[C:34]([C:31]1[CH:30]=[CH:29][C:28]([O:27][CH2:26][CH:25]([NH:24][C:22](=[O:23])[CH2:21][CH:17]2[CH2:18][CH2:19][CH2:20][CH:16]2[NH:15][C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH3:36])=[CH:33][CH:32]=1)#[N:35]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
0.4 g of N-methyhnorpholine, and subsequently 0.5 g of isopropyl chloroformate were added to a suspension containing 1.2 g of 2-amino-N-[2-(4-cyanophenoxy)-1-methylethyl]cyclopentylacetic acid amide 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 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 colorless plated crystal (yield: 90%).
Workup
- washAfter the methylene chloride layer was washed with water
- dry with materialthe organic layer was dried over anhydrous magnesium sulfate
- customthe methylene chloride was removed under reduced pressure
- customThe residue was purified by column chromatography on silica gel
Sources & evidence
- ORD record
- ord-d6c3a0e6fb4c4ef08c4559533a8547cd
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05574064
Reaction notes
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