Triethylamine → HCID 86608520, compound

HRID 2104199Notes

Reaction equation

HRID 2104199 reaction equation
[C:1]([O:9][CH:10]([CH2:54][CH3:55])[CH:11]([CH3:53])[CH:12]1[O:52][CH:13]1[CH2:14][CH:15]([CH3:51])/[CH:16]=[CH:17]/[CH:18]=[C:19](\[CH3:50])/[CH:20]1[O:32][C:30](=[O:31])[CH2:29][CH:28]([O:33][Si:34]([CH2:39][CH3:40])([CH2:37][CH3:38])[CH2:35][CH3:36])[CH2:27][CH2:26][C:25]([O:42][CH:43]([O:45][CH2:46][CH3:47])[CH3:44])([CH3:41])[CH:24]([OH:48])[CH:23]=[CH:22][CH:21]1[CH3:49])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.ClC(O[C:76]1[CH:81]=[CH:80][C:79]([N+:82]([O-:84])=[O:83])=[CH:78][CH:77]=1)=O.[C:85]([O:88]CC)(=[O:87])C>C(Cl)Cl>[C:1]([O:9][CH:10]([CH2:54][CH3:55])[CH:11]([CH3:53])[CH:12]1[O:52][CH:13]1[CH2:14][CH:15]([CH3:51])/[CH:16]=[CH:17]/[CH:18]=[C:19](\[CH3:50])/[CH:20]1[O:32][C:30](=[O:31])[CH:29]([C:85]([OH:88])=[O:87])[CH:28]([O:33][Si:34]([CH2:35][CH3:36])([CH2:39][CH3:40])[CH2:37][CH3:38])[CH2:27][CH2:26][C:25]([O:42][CH:43]([O:45][CH2:46][CH3:47])[CH3:44])([CH3:41])[CH:24]([O:48][C:76]2[CH:81]=[CH:80][C:79]([N+:82]([O-:84])=[O:83])=[CH:78][CH:77]=2)[CH:23]=[CH:22][CH:21]1[CH3:49])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 218852-DimethylaminopyridineHCID 821294-Nitrophenyl chloroformate2×HCID 86608519HCID 86608519, compound

Product 1

HCID 86608520HCID 86608520, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(8E,12E,14E)-21-benzoyloxy-6-(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-3-triethylsiloxy-18,19-epoxytricosa-8,12,14-trien-11-olide (57.1 mg, 72.7 μmol) was dissolved in methylene chloride (0.5 mL). Triethylamine (51.0 μL, 366 μmol) and dimethylaminopyridine (4.9 mg, 40.1 μmol) was added to the solution, and the reaction solution was cooled to 0° C. A solution of 4-nitrophenyl chloroformate (45.0 mg, 223 μmol) in methylene chloride (0.5 mL) was added to the solution. The reaction solution was warmed to room temperature and stirred for five hours. 4-Nitrophenyl chloroformate (17.8 mg, 88.3 μmol) was further added to the reaction solution, and the solution was stirred at the same temperature for two hours. The reaction solution was diluted with ethyl acetate (30 mL), and the dilution was washed with saturated aqueous solution of sodium hydrogencarbonate (10 mL) twice, purified water (10 mL) twice, and brine (10 mL). The resulting organic layer was dried over sodium sulfate, and then filtered. The filtrate was concentrated. The concentrate was purified by silica gel column chromatography (MERCK Silica gel 60, 63 to 200 μm; hexane:ethyl acetate=9:1) to obtain the title compound (106.6 mg) as a mixture.

Workup

  1. temperatureThe reaction solution was warmed to room temperature
  2. stirringthe solution was stirred at the same temperature for two hours
  3. washthe dilution was washed with saturated aqueous solution of sodium hydrogencarbonate (10 mL) twice
  4. custompurified water (10 mL) twice
  5. dry with materialThe resulting organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. customThe concentrate was purified by silica gel column chromatography (MERCK Silica gel 60, 63 to 200 μm; hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-3aee85834e6c4577970337fb030b3578
Source dataset
uspto-grants-2009_08
Patent number
US07576204B2

Reaction notes

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