Sodium Hydroxide → (+/-)-cis-4-(2-Amino-6-((2-hydroxy-1-(hydroxymethyl)ethyl)amino)-9H-purin-9-yl)-2-cyclopentene-1-methanol

HRID 728664

反応式

HRID 728664 の反応式
Cl.[NH2:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5].[NH2:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[CH:14][N:15]2[C@@H:18]2[CH2:22][C@H:21]([CH2:23][OH:24])[CH:20]=[CH:19]2)=[C:11](Cl)[N:10]=1.[OH-].[Na+]>CO>[NH2:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[CH:14][N:15]2[C@@H:18]2[CH2:22][C@H:21]([CH2:23][OH:24])[CH:20]=[CH:19]2)=[C:11]([NH:2][CH:3]([CH2:6][OH:7])[CH2:4][OH:5])[N:10]=1

参加物

5

反応条件

温度
80 °C

実験手順

A solution of serinol hydrochloride (0.765 g, 6.00 mmol) in methanol (20 mL) was stirred with basic ion exchange resin for 10 minutes. The resin was filtered off and the filtrate concentrated to a colorless oil. To this was added (±)-cis-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol (0.544 g, 2.00 mmol) and methanol (10 mL). The resulting solution was stirred in a Parr bomb at 80° C. overnight. 1N NaOH (2 mL) was added and the solvent evaporated. The residue was chromatrographed on silica gel. Title compound eluted with 20% methanol-chloroform; white powder after crystallization from acetonitrile-methanol (0.404 g, 63%), m.p. 160-162° C.

後処理

  1. filtrationThe resin was filtered off
  2. concentrationthe filtrate concentrated to a colorless oil
  3. customthe solvent evaporated
  4. washTitle compound eluted with 20% methanol-chloroform
  5. customwhite powder after crystallization from acetonitrile-methanol (0.404 g, 63%), m.p. 160-162° C.

出典と根拠

ORDレコード
ord-e235de0dbce9486f8b16ceb6b86aa1a9
出典データセット
uspto-grants-1991_09
特許番号
US05049671

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