Ammonia → (8E,12E,14E)-7-Carbamoyloxy-3,6,21-tri(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olide

HRID 1446647Notes

Reaction equation

HRID 1446647 reaction equation
[NH3:1].[CH2:2]([O:4][CH:5]([O:7][CH:8]1[CH2:20][CH2:19][C:18]([O:22][CH:23]([O:25][CH2:26][CH3:27])[CH3:24])([CH3:21])[CH:17]([O:28][C:29]2C=CC([N+]([O-])=O)=CC=2)[CH:16]=[CH:15][CH:14]([CH3:38])[CH:13](/[C:39](/[CH3:60])=[CH:40]/[CH:41]=[CH:42]/[CH:43]([CH3:59])[CH2:44][CH:45]2[O:58][CH:46]2[CH:47]([CH3:57])[CH:48]([O:51][CH:52]([O:54][CH2:55][CH3:56])[CH3:53])[CH2:49][CH3:50])[O:12][C:10](=[O:11])[CH:9]1C(O)=O)[CH3:6])[CH3:3].C(OCC)(=O)C.[OH2:70]>O1CCCC1>[C:29]([O:28][CH:17]1[C:18]([O:22][CH:23]([O:25][CH2:26][CH3:27])[CH3:24])([CH3:21])[CH2:19][CH2:20][CH:8]([O:7][CH:5]([O:4][CH2:2][CH3:3])[CH3:6])[CH2:9][C:10]([O:12][CH:13](/[C:39](/[CH3:60])=[CH:40]/[CH:41]=[CH:42]/[CH:43]([CH3:59])[CH2:44][CH:45]2[O:58][CH:46]2[CH:47]([CH3:57])[CH:48]([O:51][CH:52]([O:54][CH2:55][CH3:56])[CH3:53])[CH2:49][CH3:50])[CH:14]([CH3:38])[CH:15]=[CH:16]1)=[O:11])(=[O:70])[NH2:1]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 8857Ethyl AcetateHCID 86604547HCID 86604547, compound

Product 1

HCID 21024033(8E,12E,14E)-7-Carbamoyloxy-3,6,21-tri(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-18,19-epoxytricosa-8,12,14-trien-11-olideYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

28% Aqueous ammonia solution (20 μL, 300 μmol) was added dropwise to a solution of the crude (8E,12E,14E)-3,6,21-tri(1-ethoxyethoxy)-6,10,12,16,20-pentamethyl-7-(4-nitrophenoxy)carboxy-18,19-epoxytricosa-8,12,14-trien-11-olide (10 mg, about 5.3 μmol) in tetrahydrofuran (1.5 mL), followed by stirring at room temperature for 3 hours. Ethyl acetate and water were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and then evaporated. The resulting residue was purified by thin layer chromatography (MERCK Silica gel 60 F254, 0.2 mm, developing solution; ethyl acetate-hexane, 1:1) to give the title compound (3.6 mg, 90%, 2 steps) as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe resulting residue was purified by thin layer chromatography (MERCK Silica gel 60 F254, 0.2 mm, developing solution; ethyl acetate-hexane, 1:1)

Sources & evidence

ORD record
ord-eb2dc692271f4d5180013ade2c952c44
Source dataset
uspto-grants-2010_02
Patent number
US07667052B2

Reaction notes

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