Triethylamine → HCID 86601417, compound

HRID 854207Notes

Reaction equation

HRID 854207 reaction equation
[CH2:1]([Si:3]([CH2:50][CH3:51])([CH:47]([CH3:49])[CH3:48])[O:4][CH:5]1[CH2:17][CH2:16][CH:15]([CH3:18])[CH:14](O)[CH:13]=[CH:12][CH:11]([CH3:20])[CH:10](/[C:21](/[CH3:46])=[CH:22]/[CH:23]=[CH:24]/[C:25]([OH:45])([CH3:44])[CH2:26][CH:27]2[O:43][CH:28]2[CH:29]([CH3:42])[CH:30]([O:33][Si:34]([CH2:40][CH3:41])([CH2:38][CH3:39])[CH:35]([CH3:37])[CH3:36])[CH2:31][CH3:32])[O:9][C:7](=[O:8])[CH2:6]1)[CH3:2].C(N(CC)CC)C.ClC([O:62][C:63]1[CH:68]=[CH:67][C:66]([N+:69]([O-:71])=[O:70])=[CH:65][CH:64]=1)=O.[C:72]([O:75]CC)(=[O:74])C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:50]([Si:3]([CH2:1][CH3:2])([CH:47]([CH3:48])[CH3:49])[O:4][CH:5]1[CH2:17][CH2:16][CH:15]([CH3:18])[CH:14]([C:72]([O:75][O:62][C:63]2[CH:64]=[CH:65][C:66]([N+:69]([O-:71])=[O:70])=[CH:67][CH:68]=2)=[O:74])[CH:13]=[CH:12][CH:11]([CH3:20])[CH:10](/[C:21](/[CH3:46])=[CH:22]/[CH:23]=[CH:24]/[C:25]([OH:45])([CH3:44])[CH2:26][CH:27]2[O:43][CH:28]2[CH:29]([CH3:42])[CH:30]([O:33][Si:34]([CH2:40][CH3:41])([CH2:38][CH3:39])[CH:35]([CH3:36])[CH3:37])[CH2:31][CH3:32])[O:9][C:7](=[O:8])[CH2:6]1)[CH3:51]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 821294-Nitrophenyl chloroformateHCID 58932232HCID 58932232, compound

Product 1

HCID 86601417HCID 86601417, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
7.5 °C

Procedure

A solution of (8E,12E,14E)-3,21-bis(diethylisopropylsiloxy)-7,16-dihydroxy-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide (271 mg, 0.3605 mmol), 4-dimethylaminopyridine (22 mg, 0.18 mmol) and triethylamine (369 mg, 3.61 mmol) in methylene chloride (5 mL) was cooled to 5° C. A solution of 4-nitrophenyl chloroformate (374 mg, 1.8 mmol) in methylene chloride (3 mL) was added dropwise to the solution, and the reaction mixture was stirred at 5 to 10° 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 resulting organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered and 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, 1:9->1:7->1:6) to obtain the title compound (319.6 mg, 97%) as a yellow pale oil.

Workup

  1. washthe organic layer was washed with an aqueous solution of sodium hydrogencarbonate
  2. washThe resulting organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated 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, 1:9->1:7->1:6)

Sources & evidence

ORD record
ord-cbec77c3ac104b1bacd7a2531c4d10fe
Source dataset
uspto-grants-2007_08
Patent number
US07256178B2

Reaction notes

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