Sodium Hydroxide → 2-Hydroxyabacavir

HRID 1684705ノート

反応式

HRID 1684705 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), 5.79 (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]20 578 +7.87°, [α]20546 +8.77°, [α]20436 +14.4°, [α]20365 +20.1°(c=0.65, 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 ethyl acetate/15:85 as a white solid foam which
  4. custom[α]20589 +7.72°, [α]20 578 +7.87°, [α]20546 +8.77°, [α]20436 +14.4°, [α]20365 +20.1°(c=0.65, methanol)

出典と根拠

ORDレコード
ord-ae2a06412b0d4b55b08730d083771a73
出典データセット
uspto-grants-1997_06
特許番号
US05641889

反応ノート

読み込み中…