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

HRID 1292676Notes

Reaction equation

HRID 1292676 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=CC2N(O)N=NC=2C=1.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 757711-HydroxybenzotriazoleHCID 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 2-[1-(4-cyanobenzyl)-1H-imidazol-5-yl]acetic acid (220 mg, 0.533 mmol) and the amine hydrochloride salt from step C (212 mg, 0.533 mmol), HOBT (72 mg, 0.533 mmol), and N-methylmorpholine (117 μl, 1.11 mmol) in DMF (2 ml) was added EDC (764 mg, 3.99 mmol). The reaction was stirred at room temperature for 72 hrs, diluted with EtOAc and the organic layer washed with sat. aq NaHCO3, brine, dried (Na2SO4). and evaporated in vacuo. The residue was chromatographed (SiO2, 3-4% MeOH in CH2Cl2, gradient elution) 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. customand evaporated in vacuo
  4. customThe residue was chromatographed
  5. wash(SiO2, 3-4% MeOH in CH2Cl2, gradient elution)

Sources & evidence

ORD record
ord-9223f5ea085644d2b537113073957443
Source dataset
uspto-grants-1998_05
Patent number
US05756528

Reaction notes

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