Diisopropylethylamine → (S)-2-{[1-(1-Cyclohexyl-2-furan-3-yl-1H-benzoimidazol-5-yl)-methanoyl]-amino}-3-(4-nitrophenyl)-propionic Acid Methyl Ester

HRID 1007690Notes

Reaction equation

HRID 1007690 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.Cl.[CH3:47][O:48][C:49](=[O:62])[C@H:50]([CH2:52][C:53]1[CH:58]=[CH:57][C:56]([N+:59]([O-:61])=[O:60])=[CH:55][CH:54]=1)[NH2:51].CCN(C(C)C)C(C)C>CS(C)=O.CC(O)=O.O>[CH3:47][O:48][C:49](=[O:62])[C@@H:50]([NH:51][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])[CH2:52][C:53]1[CH:58]=[CH:57][C:56]([N+:59]([O-:61])=[O:60])=[CH:55][CH:54]=1

Participants

8

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 11715866Methyl 4-nitro-L-phenylalaninate hydrochloride

Product 1

HCID 69314430(S)-2-{[1-(1-Cyclohexyl-2-furan-3-yl-1H-benzoimidazol-5-yl)-methanoyl]-amino}-3-(4-nitrophenyl)-propionic Acid Methyl EsterYield 92%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

The carboxylic acid of example 2 (0.500 g, 1.61 mmol), TBTU (0.621 g, 1.94 mmol) and 4-nitro-L-phenylalanine methyl ester hydrochloride (0.461 g, 1.77 mmol) were dissolved in DMSO (2.0 mL) and DIEA (6.44 mmol, 1.12 mL) was added. The mixture was stirred for 2 h at room temperature (HPLC: complete). The reaction mixture was added dropwise with stirring to a mixture of water (45 mL) and AcOH (0.8 mL). The precipitate that formed was collected by filtration, washed with water and dried (0.768 g, 92% yield).

Workup

  1. additionThe reaction mixture was added dropwise
  2. customThe precipitate that formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried (0.768 g, 92% yield)

Sources & evidence

ORD record
ord-45760c7c2a8c445a84c8af3cba7fc9b6
Source dataset
uspto-grants-2004_09
Patent number
US06794404B2

Reaction notes

Loading…