Ammonium Chloride → 2-Propanyl 4-[(3S,5aR,6R,7R,8aS)-6-[(1E)-3-oxo-4-phenoxy-1-buten-1-yl]-7-(tetrahydro-2H-pyran-2-yloxy)octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate

HRID 1915207노트

반응식

HRID 1915207 반응식
COP([CH2:7][C:8](=[O:17])[CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=O)OC.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[CH:26]([C@@H:28]1[C@@H:37]2[C@@H:31]([O:32][CH2:33][C@@H:34]([CH2:38][CH2:39][CH2:40][C:41]([O:43][CH:44]([CH3:46])[CH3:45])=[O:42])[CH2:35][CH2:36]2)[CH2:30][C@H:29]1[O:47][CH:48]1[CH2:53][CH2:52][CH2:51][CH2:50][O:49]1)=O.[Cl-].[NH4+]>C1COCC1>[O:17]=[C:8]([CH2:9][O:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)/[CH:7]=[CH:26]/[C@@H:28]1[C@@H:37]2[C@@H:31]([O:32][CH2:33][C@@H:34]([CH2:38][CH2:39][CH2:40][C:41]([O:43][CH:44]([CH3:45])[CH3:46])=[O:42])[CH2:35][CH2:36]2)[CH2:30][C@H:29]1[O:47][CH:48]1[CH2:53][CH2:52][CH2:51][CH2:50][O:49]1

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 580104Dimethyl 2-oxo-3-phenoxypropylphosphonateHCID 866653202-Propanyl 4-[(3S,5aR,6R,7R,8aS)-6-formyl-7-(tetrahydro-2H-pyran-2-yloxy)octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate

생성물 1

HCID 687522552-Propanyl 4-[(3S,5aR,6R,7R,8aS)-6-[(1E)-3-oxo-4-phenoxy-1-buten-1-yl]-7-(tetrahydro-2H-pyran-2-yloxy)octahydro-2H-cyclopenta[b]oxepin-3-yl]butanoate수율 50.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Under the argon atmosphere, dimethyl-(3-phenoxy-2-oxopropyl)-phosphonate (826 mg, 3.20 mmol) and potassium phosphate (679 mg, 3.20 mmol) were added to a THF solution (16 mL) of the compound (634 mg, 1.60 mmol) produced in Example 13, and the mixture was stirred at room temperature for one day. The reaction solution was added to an aqueous saturated ammonium chloride solution, and the aqueous layer was extracted with ethyl acetate two times. The collected organic layers were washed with a saturated saline, and dried with anhydrous sodium sulfate. The solution was concentrated under reduced pressure, and purified with a column apparatus (Hiflash-SI, Size L, hexane→ethyl acetate:hexane=4:6) manufactured by Yamazen Corporation to obtain a titled compound (426 mg) having the following physical property values.

후처리

  1. extractionthe aqueous layer was extracted with ethyl acetate two times
  2. washThe collected organic layers were washed with a saturated saline
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationThe solution was concentrated under reduced pressure
  5. custompurified with a column apparatus (Hiflash-SI, Size L, hexane→ethyl acetate:hexane=4:6)

출처 및 근거

ORD 기록
ord-a74dd5a74f1c448ebd6e996f7f219f4f
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614340B2

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