Palmitic Acid → HCID 57642037, compound

HRID 2112423Notes

Reaction equation

HRID 2112423 reaction equation
Cl.CN(C)CCCN=C=NCC.[CH3:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([OH:30])=O.FC(F)(F)C([O-])=O.[NH:38]1[CH2:43][CH2:42][CH:41]([CH2:44][CH2:45][O:46][N:47]2[C:55](=[O:56])[C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[C:48]2=[O:57])[CH2:40][CH2:39]1.C(N(C(C)C)C(C)C)C>CN(C)C=O.ClCCl.C(OCC)(=O)C>[C:28]([N:38]1[CH2:39][CH2:40][CH:41]([CH2:44][CH2:45][O:46][N:47]2[C:55](=[O:56])[C:54]3[C:49](=[CH:50][CH:51]=[CH:52][CH:53]=3)[C:48]2=[O:57])[CH2:42][CH2:43]1)(=[O:30])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13]

Participants

9

Reactant 5

HCID 985Palmitic AcidHCID 81531DiisopropylethylamineHCID 84468TrifluoroacetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57642056HCID 57642056, compound

Product 1

HCID 57642037HCID 57642037, compoundYield 54.5%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.04 g, 5.44 mmol) was added to a solution of palmic acid (1.40 g, 5.44 mmol) and 3,4-dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazole (0.89 g, 5.44 mmol) in N,N-dimethylformamide (20 ml) and dichloromethane (20 ml). The reaction mixture was stirred at 0° C. for 20 min. A solution of the trifluoroacetate salt of 2-(2-(piperidin-4-yl)ethoxy)isoindole-1,3-dione (2.11 g, 5.44 mmol) in N,N-dimethylformamide (5 ml) and ethyldiisopropylamine (6.19 ml, 38.1 mmol) were added successively. The reaction mixture was stirred for 16 h, while it was warming up to room temperature. It was diluted with ethyl acetate (150 ml) and was washed with a 10% aqueous solution of sodium hydrogensulphate (150 ml). The aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with a mixture of water (50 ml) and a saturated aqueous solution of sodium hydrogencarbonate (50 ml) and dried over magnesium sulphate. The crude product was purified by flash chromatography on silica (40 g), using ethyl acetate/heptane 1:1 as eluent to give 1.52 g of 2-[2-(1-(hexadecanoyl)piperidin-4-yl)ethoxy]isoindole-1,3-dione.

Workup

  1. stirringThe reaction mixture was stirred for 16 h, while it
  2. temperaturewas warming up to room temperature
  3. washwas washed with a 10% aqueous solution of sodium hydrogensulphate (150 ml)
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washThe combined organic layers were washed with a mixture of water (50 ml)
  6. dry with materiala saturated aqueous solution of sodium hydrogencarbonate (50 ml) and dried over magnesium sulphate
  7. customThe crude product was purified by flash chromatography on silica (40 g)

Sources & evidence

ORD record
ord-c2455dc0477047568736f0290a09e38f
Source dataset
uspto-grants-2009_04
Patent number
US07524813B2

Reaction notes

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