Triethylamine → HCID 86602608, compound

HRID 1987541Notes

Reaction equation

HRID 1987541 reaction equation
[CH2:1]([O:3][CH:4]([O:6][CH:7]1[CH2:19][CH2:18][C:17]([O:21][CH:22]([O:24][CH2:25][CH3:26])[CH3:23])([CH3:20])[CH:16]([OH:27])[CH:15]=[CH:14][CH:13]([CH3:28])[CH:12](/[C:29](/[CH3:56])=[CH:30]/[CH:31]=[CH:32]/[C:33]([O:50][CH:51]([O:53][CH2:54][CH3:55])[CH3:52])([CH3:49])[CH2:34][CH:35]2[O:48][CH:36]2[CH:37]([CH3:47])[CH:38]([O:41][CH:42]([O:44][CH2:45][CH3:46])[CH3:43])[CH2:39][CH3:40])[O:11][C:9](=[O:10])[CH2:8]1)[CH3:5])[CH3:2].C(N(CC)CC)C.ClC(O[C:68]1[CH:73]=[CH:72][C:71]([N+:74]([O-:76])=[O:75])=[CH:70][CH:69]=1)=O.[C:77]([O:80]CC)(=[O:79])C>ClCCl>[CH2:1]([O:3][CH:4]([O:6][CH:7]1[CH2:19][CH2:18][C:17]([O:21][CH:22]([O:24][CH2:25][CH3:26])[CH3:23])([CH3:20])[CH:16]([O:27][C:68]2[CH:73]=[CH:72][C:71]([N+:74]([O-:76])=[O:75])=[CH:70][CH:69]=2)[CH:15]=[CH:14][CH:13]([CH3:28])[CH:12](/[C:29](/[CH3:56])=[CH:30]/[CH:31]=[CH:32]/[C:33]([O:50][CH:51]([O:53][CH2:54][CH3:55])[CH3:52])([CH3:49])[CH2:34][CH:35]2[O:48][CH:36]2[CH:37]([CH3:47])[CH:38]([O:41][CH:42]([O:44][CH2:45][CH3:46])[CH3:43])[CH2:39][CH3:40])[O:11][C:9](=[O:10])[CH:8]1[C:77]([OH:80])=[O:79])[CH3:5])[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 821294-Nitrophenyl chloroformateHCID 86602606HCID 86602606, compound

Product 1

HCID 86602608HCID 86602608, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (8E,12E,14E)-3,6,16,21-tetrakis(1-ethoxyethoxy)-7-hydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (139 mg, 0.17 mmol) in dichloromethane (2.5 mL) were added triethylamine (88 mg, 0.87 mmol), N,N-dimethylaminopyridine (64 mg, 0.52 mmol) and 4-nitrophenyl chloroformate (105 mg, 0.52 mmol) under ice cooling, followed by stirring at room temperature under nitrogen atmosphere for one hour. The reaction mixture was diluted with ethyl acetate, and then washed with a saturated aqueous solution of sodium bicarbonate and brine. The organic layer was dried over anhydrous magnesium sulfate, filtrated and evaporated. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 100 μm; ethyl acetate:hexane=20:80) to give the title compound (134 mg, 80%) as a colorless oil.

Workup

  1. washwashed with a saturated aqueous solution of sodium bicarbonate and brine
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltrated
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 100 μm; ethyl acetate:hexane=20:80)

Sources & evidence

ORD record
ord-9acfb8225ba94e8a9e7b5a10eca4894f
Source dataset
uspto-grants-2009_06
Patent number
US07550503B2

Reaction notes

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