Hydrochloric Acid → 2-[2-(4-Chloro-phenylamino)-acetylamino]-4-methyl-pentanoic acid cyanomethyl-amide

HRID 276715Notes

Reaction equation

HRID 276715 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]([OH:12])=O)=[CH:4][CH:3]=1.[NH2:13][C@H:14]([C:19]([NH:21][CH2:22][C:23](O)=O)=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17].Cl.C1C=CC2N(O)N=[N:33]C=2C=1>CN(C)C=O.C(N(CC)CC)C>[C:23]([CH2:22][NH:21][C:19](=[O:20])[CH:14]([NH:13][C:10](=[O:12])[CH2:9][NH:8][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[CH2:15][CH:16]([CH3:18])[CH3:17])#[N:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 757711-HydroxybenzotriazoleHCID 97364Leu-GlyHCID 2307172-((4-Chlorophenyl)amino)acetic acid

Product 1

HCID 874553532-[2-(4-Chloro-phenylamino)-acetylamino]-4-methyl-pentanoic acid cyanomethyl-amide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

(4-Chloro-phenylamino)-acetic acid (0.5 g) and H-Leu-Gly((CN).HCl (0.55 g) are dissolved in dimethylformamide (4 ml). HOBt (0.44 g), WSCD.HCI (0.54 g), triethylamine (0.37 ml) is added and the reaction mixture is stirred for 18 hours. After evaporation of the solvent, the residue is extracted with ethyl acetate. The extract is washed with 10% citric acid, brine, sodium bicarbonate, brine and dried over magnesium sulfate and evaporated. The crude product is slurried in diethylether and the solid filtered of and dried (vacuum) yielding a white powder with mp. 131-134° C.

Workup

  1. customAfter evaporation of the solvent
  2. extractionthe residue is extracted with ethyl acetate
  3. washThe extract is washed with 10% citric acid, brine, sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. filtrationthe solid filtered of and
  7. customdried (vacuum)
  8. customyielding a white powder with mp. 131-134° C.

Sources & evidence

ORD record
ord-2b7e6c65f7ab4df38e565224e16e81c4
Source dataset
uspto-grants-2002_03
Patent number
US06353017B1

Reaction notes

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