HOAt → Diisopropylethylamine

HRID 2287907Notes

Reaction equation

HRID 2287907 reaction equation
[C:1](OC(NC(C)(C)C/C=C/C(O)=O)=O)(C)([CH3:3])[CH3:2].ON1[C:23]2[N:24]=[CH:25][CH:26]=C[C:22]=2N=N1.Cl.[CH2:29](N=C=NCCCN(C)C)C>C(Cl)Cl>[CH:1]([N:24]([CH:23]([CH3:22])[CH3:29])[CH2:25][CH3:26])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 10847814(2E)-5-(tert-Butyloxycarbonylamino)-5-methylhex-2-enoic acid

Product 1

HCID 81531DiisopropylethylamineYield 250%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2E)-5-(tert-butyloxycarbonylamino)-5-methylhex-2-enoic acid (0.35 g, 1.42 mmol) in methylene chloride (5 ml) was added a mixture of 1-hydroxy-7-azabenzotriazole (0.193 g, 1.42 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (0.272 g, 1.42 mmol) and stirred for 30 min. Then a mixture of the obtained crude (2R)-N-[(1R)-1-(N',N'-dimethylhydrazinocarbonyl)-2-phenylethyl]-N-methyl-2-(methylamino)-3-(2-naphthyl)propionamide and diisopropylethylamine (0.61 ml, 3.55 mmol) was added and the mixture was stirred overnight. The mixture was concentrated in vacuo and chromatographed on silica (40 g) with ethyl acetate (95):methanol/10% ammonia (5) to give 0.37 g of ((3E)4-[N-((1R)-1-(N-[(1R)-1-(N',N'-dimethylhydrazinocarbonyl)-2-phenylethyl]-N-methylcarbamoyl)-2-(2-naphthyl)ethyl)-N-methylcarbamoyl]-1,1-dimethylbut-3-enyl)carbamic acid tert-butyl ester as an oil.

Workup

  1. additionThen a mixture of the

Sources & evidence

ORD record
ord-bbfbb560bdf141f4b488f0fa3456aa4f
Source dataset
uspto-grants-2000_07
Patent number
US06083908

Reaction notes

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