Sodium Hydroxide → 2-Hydroxyabacavir

HRID 581223ノート

反応式

HRID 581223 の反応式
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][C@H:14]([OH:16])[C@@H:13]([CH2:17][OH:18])[CH2:12]2)=[C:4](Cl)[N:3]=1.[CH:20]1([NH2:23])[CH2:22][CH2:21]1.[OH-].[Na+]>C(O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][C@H:14]([OH:16])[C@@H:13]([CH2:17][OH:18])[CH2:12]2)=[C:4]([NH:23][CH:20]2[CH2:22][CH2:21]2)[N:3]=1

参加物

5

反応物 3

HCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 11108834HCID 11108834、化合物

生成物 1

HCID 99484072-Hydroxyabacavir

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

(+)-(1S,2R,4R)-4-(2-Amino-6-chloro-9H-purin-9-yl)-2-(hydroxymethyl)cyclopentanol (425 mg, 1.5 mmol), cyclopropylamine (Aldrich, 1.4 mL), and ethanol (4 mL) were refluxed for 3 hours. To the cooled solution was added 1N sodium hydroxide (1.5 mL). The residual oil left on evaporation of volatiles under vacuum was chromatographed on silica gel. Title compound was eluted with methanol:ethyl acetate/15:85 as a white solid foam which solidified to white powder in methanol-acetonitrile (309 mg, 68%); m.p. 174-176° C.; mass spectrum (Cl, CH4) 305 (M+1); 1H-NMR(DMSO-d6)δ: 7.79 (s, 1, H-8); 7.25 (d, J=2.9 Hz, 1, NH), 579 (s, 2, NH2), 4.90-4.75 (m, 1, CH--N), 4.73 (d, J=4.0 Hz, 1, OH), 4.63 (t, J=5.3 Hz, 1, CHOH), 4.08-4.00 (m, 1, CHO), 3.58-3.38 (m, 2, CH2O), 3.05-2.95 (m, 1 CH--NH), 2.35-2.20 (m, 1, CH), 2.18-2.0 (m, 1, 1/2CH2), 2.0-1.9 (m, 2, methylene), 1.7-1.5 (m, 1, 1/2CH2), 0.70-0.50 (m, 4, 2CH2 of cyclopropyl); [α]20589 +7.72°, [α]20546 +8.77°, [α]20436 +14.4°; [α]20365 +20.1° (c=0.66, methanol).

後処理

  1. waitThe residual oil left on evaporation of volatiles under vacuum
  2. customwas chromatographed on silica gel
  3. washTitle compound was eluted with methanol

出典と根拠

ORDレコード
ord-ccd376859d264da1a5b76707711aa704
出典データセット
uspto-grants-1999_07
特許番号
US05919941

反応ノート

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