Diisopropylethylamine → (S)-3-(4-Cyanophenyl)-2-{(1-(1-cyclohexyl-2-furan-3-yl-1H-benzoimidazol-5-yl)-methanoyl]-amino}-propionic acid ethyl ester

HRID 1018244Notes

Reaction equation

HRID 1018244 reaction equation
[CH:1]1([N:7]2[C:11]3[CH:12]=[CH:13][C:14]([C:16](O)=[O:17])=[CH:15][C:10]=3[N:9]=[C:8]2[C:19]2[CH:23]=[CH:22][O:21][CH:20]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.[CH2:56]([O:58][C:59](=[O:71])[C@H:60]([CH2:62][C:63]1[CH:68]=[CH:67][C:66]([C:69]#[N:70])=[CH:65][CH:64]=1)[NH2:61])[CH3:57]>CS(C)=O>[CH2:56]([O:58][C:59](=[O:71])[C@@H:60]([NH:61][C:16]([C:14]1[CH:13]=[CH:12][C:11]2[N:7]([CH:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[C:8]([C:19]3[CH:23]=[CH:22][O:21][CH:20]=3)=[N:9][C:10]=2[CH:15]=1)=[O:17])[CH2:62][C:63]1[CH:68]=[CH:67][C:66]([C:69]#[N:70])=[CH:65][CH:64]=1)[CH3:57]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 4911131-Cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 69316049(s)-4-Cyanophenylalanine ethyl ester hydrochloride

Product 1

HCID 59909984(S)-3-(4-Cyanophenyl)-2-{(1-(1-cyclohexyl-2-furan-3-yl-1H-benzoimidazol-5-yl)-methanoyl]-amino}-propionic acid ethyl esterYield 79.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The carboxylic acid of example 2 (0.060 g, 0.20 mmol) and TBTU (1.3 equiv., 0.26 mmol, 0.084 g) were dissolved in DMSO (0.6 mL) and DIEA (5 equiv., 1.0 mmol, 0.18 mL) was added followed by (S)-4-cyanophenylalanine ethyl ester hydrochloride (1.3 equiv., 0.26 mmol, 0.065 g). The mixture was stirred at room temperature for 1 h and quenched with water. The precipitated solid was collected by filtration, washed with water and dried. The title amide (0.081 g) was obtained as a beige solid.

Workup

  1. customquenched with water
  2. filtrationThe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-7662c7ec51de42a797db851d99a37151
Source dataset
uspto-grants-2002_11
Patent number
US06479508B1

Reaction notes

Loading…