Dimethylformamide → 1-(4-cyanobenzyl)-5-[N-((carbomethoxy)-methyl)-N-(2-((tert-butoxycarbonyl)amino)acetamido)aminomethyl]imidazole

HRID 580887Notes

Reaction equation

HRID 580887 reaction equation
COC(C1C=CN=CC=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]#[N:19])=[CH:14][CH:13]=1)=O.[C:20]([NH:27][CH2:28][C:29]([OH:31])=O)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].CC[N:34]=[C:35]=[N:36][CH2:37][CH2:38][CH2:39][N:40]([CH3:42])C.Cl.C[CH2:45][O:46][C:47](C)=[O:48].C[N:51](C=O)C>>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([CH2:11][N:34]2[C:38]([CH2:39][N:40]([CH2:42][C:47]([O:46][CH3:45])=[O:48])[NH:51][C:29](=[O:31])[CH2:28][NH:27][C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])=[CH:37][N:36]=[CH:35]2)=[CH:17][CH:16]=1)#[N:19]

Participants

6

Reactant 5

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 78288N-(tert-butoxycarbonyl)glycineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 539534263-(4-Cyanobenzyl)pyridin-4-carboxylic acid methyl ester

Product 1

HCID 1317212921-(4-cyanobenzyl)-5-[N-((carbomethoxy)-methyl)-N-(2-((tert-butoxycarbonyl)amino)acetamido)aminomethyl]imidazole

Procedure

To a solution of the product of Step A (750 mg, 2.64 mmol) and Boc-glycine (462 mg, 2.64 mmol) in 10 mL of DMF was added HOBt ·H2O (392 mg, 2.9 mmol) and EDC·HCl (556 mg, 2.9 mmol). The reaction was stirred at room temperature for 2.5 hours. The solution was poured into EtOAc and washed with sat. aq. NaHCO3 soln., and brine, then dried (Na2SO4), filtered, and concentrated in vacuo. The resulting titled product was used in the next step without further purification.

Workup

  1. washwashed with sat. aq. NaHCO3 soln
  2. dry with material, and brine, then dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting titled product was used in the next step without further purification

Sources & evidence

ORD record
ord-7a0adee28164406db0e50164f85fbf33
Source dataset
uspto-grants-1999_07
Patent number
US05919785

Reaction notes

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