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 1446647노트

반응식

HRID 1446647 반응식
[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]

참가 물질

6

반응물 4

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

생성물 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-olide수율 90%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-eb2dc692271f4d5180013ade2c952c44
출처 데이터셋
uspto-grants-2010_02
특허 번호
US07667052B2

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