Hydrochloric Acid → 4-{[tert-Butyl(diphenyl)silyl]oxy}-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid

HRID 56871노트

반응식

HRID 56871 반응식
[Si:1]([O:18][CH2:19][CH2:20][CH:21]([N:32]1[CH:37]=[C:36]([O:38][CH3:39])[C:35]([C:40]2[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:41]=2[C:47]#[N:48])=[CH:34][C:33]1=[O:49])[C:22]([O:24]CC1C=CC=CC=1)=[O:23])([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].Cl>O1CCCC1>[Si:1]([O:18][CH2:19][CH2:20][CH:21]([N:32]1[CH:37]=[C:36]([O:38][CH3:39])[C:35]([C:40]2[CH:45]=[C:44]([Cl:46])[CH:43]=[CH:42][C:41]=2[C:47]#[N:48])=[CH:34][C:33]1=[O:49])[C:22]([OH:24])=[O:23])([C:14]([CH3:15])([CH3:16])[CH3:17])([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 123319622Benzyl 4-{[tert-butyl(diphenyl)silyl]oxy}-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoate

생성물 1

HCID 1239123964-{[tert-Butyl(diphenyl)silyl]oxy}-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoic acid

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

605 mg (875 μmol) of benzyl 4-{[tert-butyl(diphenyl)silyl]oxy}-2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]butanoate (racemate) were dissolved in 6 ml of tetrahydrofuran, and 2.2 ml (2.2 mmol, 2.5 eq.) of aqueous sodium hydroxide solution (1.0M) were added. The mixture was stirred at RT for another 1 h and then neutralized with aqueous hydrochloric acid (1N). The phases were separated and the aqueous phase was extracted twice with 25 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. The crude product was used for the next step without further purification. Yield: 568 mg (93% of theory)

후처리

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted twice with 25 ml of ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure
  6. customThe crude product was used for the next step without further purification

출처 및 근거

ORD 기록
ord-d538ff6c113940e8aa473144076f8827
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434690B2

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