tert-Butanol → HCID 46871039, compound

HRID 534704Notes

Reaction equation

HRID 534704 reaction equation
C(O)(C)(C)C.[CH3:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]/[CH:19]=[CH:20]/[C@@H:21]([OH:26])[C@@H:22]([NH2:25])[CH2:23][OH:24].Cl.[CH:28]1([C:34](O)=[O:35])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1.C1(N=C=NC2CCCCC2)CCCCC1.CN1CCOCC1>O1CCCC1>[OH:24][CH2:23][C@H:22]([NH:25][C:34]([CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:35])[C@H:21]([OH:26])/[CH:20]=[CH:19]/[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH3:6]

Participants

7

Reactant 5

HCID 6386tert-ButanolHCID 7413Cyclohexanecarboxylic acidHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 17998971HCID 17998971, compound

Product 1

HCID 46871039HCID 46871039, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-((2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl)cyclohexanecarboxamide (Compound I-1) was synthesized by adding 40 mg (0.29 mmol) of tert-butyl alcohol (HOBt) and 100 mg (0.29 mmol) of D-sphingosine/HCl at 0° C. to the solution of 38 mg (0.29 mmol) of cyclohexanecarboxylic acid in 25 mL of anhydrous tetrahydrofuran (THF). After 5 min, 67 mg (0.33 mmol) of dicyclohexylcarbodiimide (DCC) was added, and the pH of the solution was adjusted to 8 with 4-methylmorpholine. The reaction mixture was stirred at 0° C. for 2 h and at room temperature overnight. On evaporation the residue was dissolved in 100 mL of ethyl acetate. The solution was washed successively with saturated sodium bicarbonate, 5% potassium bisulfate, and saturated sodium chloride, and the organic phase was separated and dried over anhydrous magnesium sulfate for 2 h. After filtration and evaporation under reduced pressure, the crude product was recrystallized in ethyl ether to obtain 60 mg (51%) of N-((2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl)cyclohexanecarboxamide as colorless powder. GC/MS (m/e): 391 [M+H2O]+. 1H NMR (d6-DMSO, 300 MHz) δ/ppm=7.224 (d, J=8.4 Hz, 1H), 5.513 (dt, J=15.3 Hz, J=6.6 Hz, 1H), 5.345 (dd, J=15.3 Hz, J=6.6 Hz, 1H), 4.789 (d, J=5.1 Hz, 1H), 4.422 (t, J=5.4 Hz, 1H), 3.872 (q, J=6.0 Hz, 1H), 3.636 (m, 1H), 3.446 (m, 2H), 2.088 (m, 1H), 1.917 (m, 2H), 1.652 (m, 6H), 1.225-1.157 (m, 26H), 0.843 (t, J=6.6 Hz, 3H). 13C NMR (d6-DMSO, 75 MHz) δ/ppm=132.083, 131.506, 72.063, 61.298, 55.665, 44.657, 32.358, 31.979, 30.172, 29.732, 29.656, 29.382, 29.246, 26.194, 26.042, 22.778, 14.624. Anal. Calcd for C25H47NO3: C, 73.30; H, 11.56; N, 3.42; O, 11.72. Found: C, 72.99; H, 11.64; N, 3.74; O, 11.91.

Workup

  1. customN-((2S,3R,E)-1,3-dihydroxyoctadec-4-en-2-yl)cyclohexanecarboxamide (Compound I-1) was synthesized
  2. customOn evaporation the residue
  3. dissolutionwas dissolved in 100 mL of ethyl acetate
  4. washThe solution was washed successively with saturated sodium bicarbonate, 5% potassium bisulfate, and saturated sodium chloride
  5. customthe organic phase was separated
  6. dry with materialdried over anhydrous magnesium sulfate for 2 h
  7. filtrationAfter filtration and evaporation under reduced pressure
  8. customthe crude product was recrystallized in ethyl ether

Sources & evidence

ORD record
ord-14e1559dbd264a3796dfdbebe453fb79
Source dataset
uspto-grants-2014_10
Patent number
US08853452B2

Reaction notes

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