Water → HCID 53853248, compound

HRID 2226571Notes

Reaction equation

HRID 2226571 reaction equation
CN1CCOCC1.Cl[C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10].Cl.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]2[O:24][C:23]([CH:25]([NH:27][C:28](=[O:34])[CH:29]([NH2:33])[CH:30]([CH3:32])[CH3:31])[CH3:26])=[CH:22][C:21]=2[CH:35]=1.O>ClCCl>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]2[O:24][C:23]([CH:25]([NH:27][C:28](=[O:34])[C@H:29]([CH:30]([CH3:31])[CH3:32])[NH:33][C:9]([O:11][CH:12]([CH3:14])[CH3:13])=[O:10])[CH3:26])=[CH:22][C:21]=2[CH:35]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7917Isopropyl chloroformateHCID 79724-MethylmorpholineHCID 18965424HCID 18965424, compound

Product 1

HCID 53853248HCID 53853248, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.54 g of N-methylmorpholine, and subsequently 0.7 g of isopropyl chloroformate were added to a solution containing 1.57 g of N-[1-(5-chloro-2-benzofuranyl)ethyl]-2-amino-3-methylbutanamide hydrochloride dissolved in 40 ml of dichloromethane 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 dichloromethane layer was washed with water, the organic layer was dried over anhydrous magnesium sulfate and then concentrated. The residue, which was a crude crystal, was purified by column chromatography on silica gel, thus obtaining 0.85 g of the desired product in the form of a white powder.

Workup

  1. washAfter the dichloromethane layer was washed with water
  2. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-bffe946daa584f158ad18a02ce745b8f
Source dataset
uspto-grants-1994_09
Patent number
US05348976

Reaction notes

Loading…