Hydrochloric Acid → (S)-2-[(phenylisopropyl)amino]adenosine

HRID 22069

반응식

HRID 22069 반응식
[C:1]1([CH:7]([NH:10][C:11]2[N:12]=[C:13]([NH2:29])[C:14]3[N:15]=[CH:16][N:17]([C:27]=3[N:28]=2)[C@@H:18]2[O:26][C@H:23]([CH2:24][OH:25])[C@@H:21]([OH:22])[C@H:19]2[OH:20])[CH2:8]C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.[C:31](=O)(O)[O-].[Na+]>>[C:1]1([C:7]([NH:10][C:11]2[N:12]=[C:13]([NH2:29])[C:14]3[N:15]=[CH:16][N:17]([C:27]=3[N:28]=2)[C@H:18]2[O:26][C@H:23]([CH2:24][OH:25])[C@@H:21]([OH:22])[C@H:19]2[OH:20])([CH3:8])[CH3:31])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

4

반응물 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 53927112(R)-2-[(1-Phenylpropyl)amino]adenosine

생성물 1

HCID 67681966(S)-2-[(phenylisopropyl)amino]adenosine

실험 절차

Treat the secondary amine (3) (0.46 g, 1.05 mmol) with 1M hydrochloric acid (40 ml) and heat the reaction to 45° C. for 15 minutes. Cool the reaction and pour into saturated sodium bicarbonate (300 ml). Extract the reaction with chloroform (3×150 ml). Combine the organic extracts, dry over anhydrous magnesium sulfate, filter, and concentrate under vacuum to provide the title compound (0.40 g) as the free base. Treat this with ethereal hydrogen chloride, filter, and dry the solid under high vacuum over phosphorous pentoxide. Recrystallize from 10% methanol/diethyl ether to provide, after drying under high vacuum over phosphorous pentoxide, the hydrochloride salt of the Formula I (184 mg), m.p. 155° C. dec.; [α]D20 =+9.75° (c=1.01, H2O).

후처리

  1. temperatureheat
  2. customthe reaction to 45° C. for 15 minutes
  3. temperatureCool
  4. customthe reaction
  5. extractionExtract
  6. customthe reaction with chloroform (3×150 ml)
  7. dry with materialCombine the organic extracts, dry over anhydrous magnesium sulfate
  8. filtrationfilter
  9. concentrationconcentrate under vacuum

출처 및 근거

ORD 기록
ord-84b9773a3a7842ed89c5ed506153bd50
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05426101

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