Triethylamine → HCID 86601414, compound

HRID 854203Notes

Reaction equation

HRID 854203 reaction equation
O[CH:2]1[CH:3]([CH3:56])[CH2:4][CH2:5][CH:6]([O:48][Si:49]([CH2:54][CH3:55])([CH2:52][CH3:53])[CH2:50][CH3:51])[CH2:7][C:8]([O:10][CH:11](/[C:16](/[CH3:47])=[CH:17]/[CH:18]=[CH:19]/[C:20]([CH3:46])([O:38][Si:39]([CH2:44][CH3:45])([CH2:42][CH3:43])[CH2:40][CH3:41])[CH2:21][CH:22]2[O:37][CH:23]2[CH:24]([CH3:36])[CH:25]([O:28][Si:29]([CH2:34][CH3:35])([CH2:32][CH3:33])[CH2:30][CH3:31])[CH2:26][CH3:27])[CH:12]([CH3:15])[CH:13]=[CH:14]1)=[O:9].C(N(CC)CC)C.ClC([O:67][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>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:56][CH:3]1[CH:2]([C:77]([O:80][O:67][C:68]2[CH:69]=[CH:70][C:71]([N+:74]([O-:76])=[O:75])=[CH:72][CH:73]=2)=[O:79])[CH:14]=[CH:13][CH:12]([CH3:15])[CH:11](/[C:16](/[CH3:47])=[CH:17]/[CH:18]=[CH:19]/[C:20]([CH3:46])([O:38][Si:39]([CH2:40][CH3:41])([CH2:44][CH3:45])[CH2:42][CH3:43])[CH2:21][CH:22]2[O:37][CH:23]2[CH:24]([CH3:36])[CH:25]([O:28][Si:29]([CH2:34][CH3:35])([CH2:30][CH3:31])[CH2:32][CH3:33])[CH2:26][CH3:27])[O:10][C:8](=[O:9])[CH2:7][CH:6]([O:48][Si:49]([CH2:54][CH3:55])([CH2:52][CH3:53])[CH2:50][CH3:51])[CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 821294-Nitrophenyl chloroformateHCID 86601413HCID 86601413, compound

Product 1

HCID 86601414HCID 86601414, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

A solution of (8E,12E,14E)-7-hydroxy-6,10,12,16,20-pentamethyl-3,16,21-tris(triethylsiloxy)-18,19-epoxytricosa-8,12,14-trien-11-olide (38.6 mg, 0.046 mmol), 4-dimethylaminopyridine (26 mg, 0.207 mmol) and triethylamine (28 mg, 0.276 mmol) in methylene chloride (2 mL) was cooled to 5° C. A solution of 4-nitrophenyl chloroformate (29 mg, 0.138 mmol) in methylene chloride (1 mL) was added to the reaction mixture, and the reaction mixture was stirred at 5° C. for one hour. The reaction mixture was diluted with ethyl acetate, and then the organic layer was washed with an aqueous solution of sodium hydrogencarbonate. The organic layer was sequentially washed with an aqueous solution of ammonium chloride, an aqueous solution of sodium hydrogencarbonate and water, dried with anhydrous magnesium sulfate, and filtered. Then, the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane, 1:14) to obtain the title compound (46.1 mg, 100%) as a yellow pale oil.

Workup

  1. washthe organic layer was washed with an aqueous solution of sodium hydrogencarbonate
  2. washThe organic layer was sequentially washed with an aqueous solution of ammonium chloride
  3. dry with materialan aqueous solution of sodium hydrogencarbonate and water, dried with anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThen, the filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (Kanto silica gel 60N, 40 to 50 μm; ethyl acetate-hexane, 1:14)

Sources & evidence

ORD record
ord-02adac1fca23451e8963cc08a0ab80e9
Source dataset
uspto-grants-2007_08
Patent number
US07256178B2

Reaction notes

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