Water → HCID 67639432, compound

HRID 1900203Notes

Reaction equation

HRID 1900203 reaction equation
[CH3:1]N1CCOCC1.Cl[C:9]([O:11][CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:10].Cl.[NH2:18][C@H:19]([C:23]([NH:25][C@H:26]([C:28]([NH:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=1)=[O:29])[CH3:27])=[O:24])[CH:20]([CH3:22])[CH3:21].O>C(Cl)Cl>[CH:12]1([O:11][C:9]([NH:18][C@H:19]([C:23]([NH:25][C@@H:26]([C:28]([NH:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=2)=[O:29])[CH3:27])=[O:24])[CH:20]([CH3:21])[CH3:22])=[O:10])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:1]1

Participants

6

Reactant 4

HCID 962WaterHCID 79724-MethylmorpholineHCID 2735892Cyclopentyl chloroformateHCID 131719640HCID 131719640, compound

Product 1

HCID 67639432HCID 67639432, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.6 g of N-methyhnorpholine, and subsequently 0.6 g of cyclopentyl chloroformate were added to a suspension containing 1.0 g of L-valyl-N-(4-cyanophenyl)alaninamide, hydrochloride suspended in 50 ml of methylene chloride at -20° 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 a white crystal (yield: 49% ).

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-042580a689df47a099b96a9750455452
Source dataset
uspto-grants-1996_11
Patent number
US05574064

Reaction notes

Loading…