Hydrochloric Acid → N-[2-t-Butyl-5-(3-hydroxypropyl)phenyl]-2-(9H-xanthen-9-yl)acetamide

HRID 977859노트

반응식

HRID 977859 반응식
CCCCCC.[H-].C([Al+]CC(C)C)C(C)C.[C:17]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][C:29](OCC)=[O:30])=[CH:23][C:22]=1[NH:34][C:35](=[O:51])[CH2:36][CH:37]1[C:50]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[O:44][C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)([CH3:20])([CH3:19])[CH3:18].Cl>O1CCCC1>[C:17]([C:21]1[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][OH:30])=[CH:23][C:22]=1[NH:34][C:35](=[O:51])[CH2:36][CH:37]1[C:50]2[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=2[O:44][C:43]2[C:38]1=[CH:39][CH:40]=[CH:41][CH:42]=2)([CH3:20])([CH3:18])[CH3:19]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8058HexaneHCID 19966227N-[2-t-butyl-5-(2-ethoxycarbonylethyl)phenyl]-2-(9H-xanthen-9-yl)acetamideHCID 21225700Diisobutylaluminumhydride

생성물 1

HCID 19966239N-[2-t-Butyl-5-(3-hydroxypropyl)phenyl]-2-(9H-xanthen-9-yl)acetamide수율 67%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

5.96 ml (5.96 mmol) of a 1.0M hexane solution of diisobutylaluminum hydride were added dropwise, over a period of 10 minutes, to 14 ml of a tetrahydrofuran solution containing 702 mg (1.49 mmol) of N-[2-t-butyl-5-(2-ethoxycarbonylethyl)phenyl]-2-(9H-xanthen-9-yl)acetamide (prepared as described in Preparation 17) which had previously been cooled at -78° C. The mixture was stirred for 75 minutes at this temperature and then for 45 minutes at room temperature. At the end of this time, the reaction solution was poured into a mixture of dilute aqueous hydrochloric acid and ice, and was then extracted with diethyl ether. The organic extract was washed with water, and then the solvent was removed by distillation under reduced pressure. The resulting residue was subjected to column chromatography through 30 g of silica gel. Elution with a 5:4 by volume mixture of methylene chloride and ethyl acetate afforded 427 mg (yield 67%) of the title compound as crystals, melting at 185°-186° C. (after recrystallization from a mixture of methylene chloride and diethyl ether).

후처리

  1. waitfor 45 minutes at room temperature
  2. extractionwas then extracted with diethyl ether
  3. extractionThe organic extract
  4. washwas washed with water
  5. customthe solvent was removed by distillation under reduced pressure
  6. washElution with a 5:4
  7. additionby volume mixture of methylene chloride and ethyl acetate

출처 및 근거

ORD 기록
ord-9b59a3f001b94cc48b2285be28a19e9b
출처 데이터셋
uspto-grants-1997_03
특허 번호
US05614550

반응 노트

불러오는 중…