Diisopropylethylamine → HCID 67806555, compound

HRID 1647869Notes

Reaction equation

HRID 1647869 reaction equation
C(N(C(C)C)C(C)C)C.[C:10]([C:12]1[CH:33]=[CH:32][C:15]([C:16]([N:18]([CH3:31])[C:19]2[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][C:20]=2[N+:28]([O-:30])=[O:29])=[O:17])=[CH:14][CH:13]=1)#[N:11].Cl.[NH2:35][CH2:36][CH2:37][CH2:38][C:39]([O:41][CH3:42])=[O:40]>C(Cl)Cl>[CH3:42][O:41][C:39]([CH2:38][CH2:37][CH2:36][NH:35][C:23](=[O:24])[C:22]1[CH:26]=[CH:27][C:19]([N:18]([CH3:31])[C:16](=[O:17])[C:15]2[CH:32]=[CH:33][C:12]([C:10]#[N:11])=[CH:13][CH:14]=2)=[C:20]([N+:28]([O-:30])=[O:29])[CH:21]=1)=[O:40]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27563834-Aminobutyric acid methyl ester hydrochlorideHCID 19921194HCID 19921194, compound

Product 1

HCID 67806555HCID 67806555, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2.84 g of N-ethyl-diisopropylamine are added, with cooling to 0° C., to a mixture of 3.2 g of 4-[N-(4-cyano-benzoyl)-methylamino]-3-nitro-benzoylchloride, 1.68 g of methyl 4-aminobutyrate-hydrochloride and 50 ml of methylene chloride. The mixture is stirred for 64 hours and allowed to return to ambient temperature. The methylene chloride is evaporated off and the residue is purified over silica gel (eluant:ethyl acetate/ethanol=200:1). Yield: 3.9 g (100% of theory), Rf value: 0.62 (silica gel; ethyl acetate/ethanol=9:1)

Workup

  1. customto return to ambient temperature
  2. customThe methylene chloride is evaporated off
  3. customthe residue is purified over silica gel (eluant:ethyl acetate/ethanol=200:1)

Sources & evidence

ORD record
ord-f283e353decd482abc2881d70e09f57a
Source dataset
uspto-grants-1995_07
Patent number
US05434150

Reaction notes

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