Water → 3-[4-{2-(4-[Tert-butoxycarbonylamino]phenyl)ethoxy}phenyl]-2-ethoxy-2-methyl-propanoic acid

HRID 987288노트

반응식

HRID 987288 반응식
[OH-].[Na+].[C:3]([O:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][O:19]S(C2C=CC(C)=CC=2)(=O)=O)=[CH:13][CH:12]=1)=[O:9])([CH3:6])([CH3:5])[CH3:4].C([O:32][C:33](=[O:47])[C:34]([O:44][CH2:45][CH3:46])([CH3:43])[CH2:35][C:36]1[CH:41]=[CH:40][C:39](O)=[CH:38][CH:37]=1)C.O>CS(C)=O.O1CCCC1>[C:3]([O:7][C:8]([NH:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][O:19][C:39]2[CH:38]=[CH:37][C:36]([CH2:35][C:34]([O:44][CH2:45][CH3:46])([CH3:43])[C:33]([OH:47])=[O:32])=[CH:41][CH:40]=2)=[CH:15][CH:16]=1)=[O:9])([CH3:4])([CH3:5])[CH3:6]

참가 물질

7

반응물 4

HCID 962WaterHCID 14798Sodium Hydroxide2회HCID 113267772-(4-(Tert-butoxycarbonylamino)phenyl]ethyl-4-methylbenzenesulfonateHCID 538891572-Ethoxy-3-(4-hydroxyphenyl)2-methyl propanoic acid ethyl ester

생성물 1

HCID 229886853-[4-{2-(4-[Tert-butoxycarbonylamino]phenyl)ethoxy}phenyl]-2-ethoxy-2-methyl-propanoic acid수율 17.6%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 8028Tetrahydrofuran용매

실험 절차

Sodium hydroxide (0.105 g; 2.63 mmole) was pulverized and dissolved in DMSO (8 ml). To 4 ml of this solution 2-[4-(tert-butoxycarbonylamino)phenyl]ethyl-4-methylbenzenesulfonate (described in Example 40a) (0.515 g; 1.316 mmole) and 2-ethoxy-3-(4-hydroxyphenyl)2-methyl propanoic acid ethyl ester (0.331 g; 1.316 mmole) were added and the mixture was stirred at room temperature over night. The remaining volume (4 ml) of the sodium hydroxide solution and water (1 ml) were added. A precipitate was formed which was dissolved by addition of tetrahydrofuran (1 ml). The mixture was allowed to stand over night and was then evaporated. The residue was redissolved in dichloromethane and water and the phases were separated. The water phase was extracted once more with dichloromethane, acidified with hydrochloric acid (1 M), extracted several times with ethyl acetate and diethyl ether. The organic phases were combined, dried with magnesium sulfate and evaporated. Purification of the crude product by flash chromatography and preparative HPLC gave 0.103 g (17.1% yield) of 3-[4-{2-(4[-tert-butoxycarbonylamino]phenyl)ethoxy}phenyl]-2-ethoxy-2-methyl-propanoic acid.

후처리

  1. customA precipitate was formed which
  2. waitto stand over night
  3. customwas then evaporated
  4. dissolutionThe residue was redissolved in dichloromethane
  5. customwater and the phases were separated
  6. extractionThe water phase was extracted once more with dichloromethane
  7. extractionextracted several times with ethyl acetate and diethyl ether
  8. dry with materialdried with magnesium sulfate
  9. customevaporated
  10. customPurification of the crude product by flash chromatography and preparative HPLC

출처 및 근거

ORD 기록
ord-fa591d7bfbc847e183870e53cd8819b6
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06630600B1

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