Water → HCID 67687482, compound

HRID 1900199Notes

Reaction equation

HRID 1900199 reaction equation
CN1CCOCC1.Cl[C:9]([O:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)=[O:10].[NH2:19][CH:20]1[CH2:24][CH2:23][CH2:22][CH:21]1[CH2:25][C:26]([NH:28][CH:29]([CH3:40])[CH2:30][O:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=1)=[O:27].O>C(Cl)Cl>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:9]([NH:19][CH:20]2[CH2:24][CH2:23][CH2:22][CH:21]2[CH2:25][C:26]([NH:28][CH:29]([CH3:40])[CH2:30][O:31][C:32]2[CH:37]=[CH:36][C:35]([C:38]#[N:39])=[CH:34][CH:33]=2)=[O:27])=[O:10])=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 1390594-Chlorophenyl chloroformateHCID 67687474HCID 67687474, compound

Product 1

HCID 67687482HCID 67687482, compoundYield 33.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.4 g of N-methylmorpholine, and subsequently 0.8 g of 4-chlorophenyl 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 0.6 g of the desired product in the form of colorless grains (yield: 30%).

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-93bcca6b0b2c4a04b7e4dbb2e8cc917a
Source dataset
uspto-grants-1996_11
Patent number
US05574064

Reaction notes

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