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

HRID 611464

反応式

HRID 611464 の反応式
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

参加物

3

反応物 2

HCID 7504BenzylamineHCID 107488Deoxycytidine hydrochloride

生成物 1

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

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b8d3db90d1494a97b3a91288e18195a4
出典データセット
uspto-grants-1999_12
特許番号
US06001611

関連ノート

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