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 1446647ノート

反応式

HRID 1446647 の反応式
[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]

参加物

6

反応物 4

HCID 222AmmoniaHCID 962WaterHCID 8857Ethyl AcetateHCID 86604547HCID 86604547、化合物

生成物 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-olide収率 90%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-eb2dc692271f4d5180013ade2c952c44
出典データセット
uspto-grants-2010_02
特許番号
US07667052B2

反応ノート

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