1,2-Dichloroethane → N-[2(S)-([1-(4-Cyanobenzyl)-1H-imidazol-5-yl]acetylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl) glycine methyl ester

HRID 267093Notes

Reaction equation

HRID 267093 reaction equation
[C:1]([C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[C:12]([CH2:13][C:14]([OH:16])=O)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].Cl.[CH3:20][O:21][C:22](=[O:43])[CH2:23][N:24]([CH2:36][C@@H:37]([NH2:42])[C@@H:38]([CH3:41])[CH2:39][CH3:40])[CH2:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1.C1C=C2C(N(O)N=NC2=CC=1)=O.CN1CCOCC1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[CH3:20][O:21][C:22](=[O:43])[CH2:23][N:24]([CH2:36][C@@H:37]([NH:42][C:14](=[O:16])[CH2:13][C:12]1[N:8]([CH2:7][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:18][CH:17]=2)[CH:9]=[N:10][CH:11]=1)[C@@H:38]([CH3:41])[CH2:39][CH3:40])[CH2:25][C:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 730263-hydroxy-1,2,3-benzotriazin-4(3H)-oneHCID 184336301-(4-Cyanobenzyl)imidazole-5-acetic acidHCID 70338221N-[2(S)-(amino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine methyl ester hydrochloride

Product 1

HCID 67572382N-[2(S)-([1-(4-Cyanobenzyl)-1H-imidazol-5-yl]acetylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl) glycine methyl ester

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [1-(4-cyanobenzyl)-1H-imidazol-5-yl]acetic acid. (4.09 g, 10.24 mmol), the amine hydrochloride salt from step E (5.07 g, 10.24 mmol), HOOBT (1.67 g, 10.24 mmol), and N-methylmorpholine (2.36 ml, 21.5 mmol) in DMF (50 ml) at 0° C., was added EDC (2.16 g, 11.26 mmol). The reaction was stirred at room temperature for 18 hrs, diluted with EtOAc and the organic layer washed with sat. aq NaHCO3, brine, dried (Na2SO4), and the solvent evaporated in vacuo. The residue was chromatographed (SiO2, 3-4% MeOH in CH2Cl2) to afford the title compound as a white solid.

Workup

  1. washthe organic layer washed with sat. aq NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. customthe solvent evaporated in vacuo
  4. customThe residue was chromatographed (SiO2, 3-4% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-caa95c38e07e4591af8d22dfde1951c7
Source dataset
uspto-grants-1997_07
Patent number
US05652257

Reaction notes

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