Triethylamine → HCID 86601410, compound

HRID 854199Notes

Reaction equation

HRID 854199 reaction equation
[CH2:1]([O:3][CH:4]([O:6][CH:7]1[CH2:19][CH2:18][CH:17]([CH3:20])[CH:16]([OH:21])[CH:15]=[CH:14][CH:13]([CH3:22])[CH:12](/[C:23](/[CH3:50])=[CH:24]/[CH:25]=[CH:26]/[C:27]([O:44][CH:45]([O:47][CH2:48][CH3:49])[CH3:46])([CH3:43])[CH2:28][CH:29]2[O:42][CH:30]2[CH:31]([CH3:41])[CH:32]([O:35][CH:36]([O:38][CH2:39][CH3:40])[CH3:37])[CH2:33][CH3:34])[O:11][C:9](=[O:10])[CH2:8]1)[CH3:5])[CH3:2].C(N(CC)CC)C.ClC(O[C:62]1[CH:67]=[CH:66][C:65]([N+:68]([O-:70])=[O:69])=[CH:64][CH:63]=1)=O.[C:71]([O:74]CC)(=[O:73])C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH2:1]([O:3][CH:4]([O:6][CH:7]1[CH2:19][CH2:18][CH:17]([CH3:20])[CH:16]([O:21][C:62]2[CH:67]=[CH:66][C:65]([N+:68]([O-:70])=[O:69])=[CH:64][CH:63]=2)[CH:15]=[CH:14][CH:13]([CH3:22])[CH:12](/[C:23](/[CH3:50])=[CH:24]/[CH:25]=[CH:26]/[C:27]([O:44][CH:45]([O:47][CH2:48][CH3:49])[CH3:46])([CH3:43])[CH2:28][CH:29]2[O:42][CH:30]2[CH:31]([CH3:41])[CH:32]([O:35][CH:36]([O:38][CH2:39][CH3:40])[CH3:37])[CH2:33][CH3:34])[O:11][C:9](=[O:10])[CH:8]1[C:71]([OH:74])=[O:73])[CH3:5])[CH3:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 821294-Nitrophenyl chloroformateHCID 86601408HCID 86601408, compound

Product 1

HCID 86601410HCID 86601410, compoundYield 85.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

(8E,12E,14E)-3,16,21-tris(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (129 mg, 182 μmol) was dissolved in methylene chloride (1 mL). Triethylamine (127 μL, 911 μmol) and 4-dimethylaminopyridine (67.0 mg, 548 μmol) were added to the reaction mixture, and the reaction mixture was stirred at room temperature for 30 minutes. A solution of 4-nitrophenyl chloroformate (112 mg, 556 μmol) in methylene chloride (1 mL) was added dropwise to this reaction mixture and the reaction mixture was stirred at room temperature for 3.5 hours. The reaction mixture was diluted with ethyl acetate (30 mL), and the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (10 mL) and purified water (10 mL) twice, and with brine (10 mL). The resulting organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The resulting concentrate was purified by silica gel column chromatography (Merck Silica gel 60, 63 to 200 μm; hexane:ethyl acetate=5:1->4:1) to obtain the title compound (137 mg, 156 μmol, 85.8%) as a colorless oil.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 3.5 hours
  2. washthe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate (10 mL)
  3. custompurified water (10 mL) twice
  4. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. concentrationThe resulting concentrate
  8. customwas purified by silica gel column chromatography (Merck Silica gel 60, 63 to 200 μm; hexane:ethyl acetate=5:1->4:1)

Sources & evidence

ORD record
ord-004aaaec308146baae11b1b5383f990d
Source dataset
uspto-grants-2007_08
Patent number
US07256178B2

Reaction notes

Loading…