Triethylamine → HCID 86746780, compound

HRID 247825Notes

Reaction equation

HRID 247825 reaction equation
[C:1]1([CH:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][NH2:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl.CN(C)CCCN=C=NCC.[CH3:35][CH:36]([C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([CH:44]([CH3:46])[CH3:45])[C:39]=1[NH:47][C:48](=[O:56])[CH2:49][P:50](=O)([O-:54])[O:51][CH2:52][CH3:53])[CH3:37]>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:45][CH:44]([C:40]1[CH:41]=[CH:42][CH:43]=[C:38]([CH:36]([CH3:35])[CH3:37])[C:39]=1[NH:47][C:48](=[O:56])[CH2:49][P:50]([NH:9][CH2:8][CH:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:54])[O:51][CH2:52][CH3:53])[CH3:46]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 775752,2-DiphenylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 86746778HCID 86746778, compound

Product 1

HCID 86746780HCID 86746780, compoundYield 18.9%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2,2-diphenylethylamine (0.45 g, 2.3 mmol) and triethylamine (0.35 mL, 2.5 mmol) in methylene chloride (10 mL) is added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDCI) (0.48 g, 2.5 mmol), followed by (±)-[2-[[2,6-bis(1-methylethyl)phenyl]amino]-2-oxoethyl]phosphonic acid, ethyl ester (Example 5) (0.74 g, 2.3 mmol). 4-Dimethylaminopyridine (DMAP) (0.1 g) is added and the solution is stirred for 48 hours at room temperature. Additional portions of triethylamine (0.1 mL) and EDCI (0.1 g) are added and stirring is continued for another 24 hours. The reaction mixture is diluted with methylene chloride, washed with water, brine, dried over magnesium sulfate, and concentrated. Flash chromatography (ethyl acetate) affords 0.22 g of the product as a white solid. Recrystallization from ethyl acetate/hexane affords 0.18 g of the title compound as a white solid; mp 172°-176° C.

Workup

  1. stirringstirring
  2. waitis continued for another 24 hours
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dfc8e88ed465468eb296f66b36573ffc
Source dataset
uspto-grants-1993_05
Patent number
US05208224

Reaction notes

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