Methanol → HCID 18997525, compound

HRID 726441Notes

Reaction equation

HRID 726441 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:5][CH:4]=1)#[N:2].CO.[CH3:19]CN=C=NCCCN(C)C.Cl>C(Cl)Cl.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH3:19][O:15][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=1

Participants

7

Reactant 3

HCID 887MethanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 18794122HCID 18794122, compound

Product 1

HCID 18997525HCID 18997525, compoundYield 56.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(p-cyanophenyl)hexanoic acid (1.0 g), which is disclosed in J. Med. Chem., 36, 1811 (1993), in methylene chloride (10 ml) are added methanol (0.2 ml), WSC.HCl (883 mg) and 4-dimethylaminopyridine (561 mg), and the mixture is stirred at room temperature for 30 minutes. The mixture is diluted with ethyl acetate, and washed with 1N hydrochloric acid and a saturated aqueous sodium hydrogen carbonate solution, and purified by silica gel column chromatography (n-hexane/ethyl acetate=5:1) to give the title compound (600 mg).

Workup

  1. washwashed with 1N hydrochloric acid
  2. customa saturated aqueous sodium hydrogen carbonate solution, and purified by silica gel column chromatography (n-hexane/ethyl acetate=5:1)

Sources & evidence

ORD record
ord-e6ff5cf55d4042cf8c961adf704b3ef1
Source dataset
uspto-grants-1998_01
Patent number
US05707994

Reaction notes

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