Benzylamine → 2'-Deoxy-N-(phenylmethyl)cytidine

HRID 611464

반응식

HRID 611464 반응식
Cl.[C@@H:2]1([N:10]2[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]2=[O:12])[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[CH2:3]1.[CH2:18](N)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[CH2:18]([NH:15][C:14]1[CH:16]=[CH:17][N:10]([C@@H:2]2[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[CH2:3]2)[C:11](=[O:12])[N:13]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

참가 물질

3

반응물 2

HCID 7504BenzylamineHCID 107488Deoxycytidine hydrochloride

생성물 1

HCID 114725832'-Deoxy-N-(phenylmethyl)cytidine

반응 조건

온도
150 °C

실험 절차

To 2'-deoxycytidine hydrochloride (5.28g, 20 mmol, U.S. Biochemical Corp., Cleveland, Ohio) was added benzylamine (20 ml), and the mixture was heated at 150° C. for 3 hours under an argon atmosphere. The solution was concentrated under vacuum to yield a viscous yellow oil, which was partitioned between water (100 ml) and ethyl acetate (100 ml). The aqueous phase was washed with ethyl acetate (100 ml) and separated. The aqueous phase was concentrated under vacuum to yield a yellow syrup (13 g), which was purified by silica gel column chromatography with 15:1 methylene chloride:methanol as eluant, to yield the desired product (5.8 g, 91.5%), as a colorless syrup.

후처리

  1. concentrationThe solution was concentrated under vacuum
  2. customto yield a viscous yellow oil, which
  3. customwas partitioned between water (100 ml) and ethyl acetate (100 ml)
  4. washThe aqueous phase was washed with ethyl acetate (100 ml)
  5. customseparated
  6. concentrationThe aqueous phase was concentrated under vacuum

출처 및 근거

ORD 기록
ord-b8d3db90d1494a97b3a91288e18195a4
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06001611

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