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Triethylamine → 2-fluoro-N-[(R)-1-phenoxy-2-propyl]adenosine

HRID 1379643
ノート
印刷プレビュー

反応式

HRID 1379643 の反応式
C([O:4][C@@H:5]1[C@H:9]([O:10]C(=O)C)[C@@H:8]([CH2:14][O:15]C(=O)C)[O:7][C@H:6]1[N:19]1[CH:27]=[N:26][C:25]2[C:20]1=[N:21][C:22]([F:29])=[N:23][C:24]=2Cl)(=O)C.[O:30]([CH2:37][C@H:38]([NH2:40])[CH3:39])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(N(CC)CC)C>O1CCOCC1>[F:29][C:22]1[N:23]=[C:24]([NH:40][C@H:38]([CH3:39])[CH2:37][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:25]2[N:26]=[CH:27][N:19]([C:20]=2[N:21]=1)[C@@H:6]1[O:7][C@H:8]([CH2:14][OH:15])[C@@H:9]([OH:10])[C@H:5]1[OH:4]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8471TriethylamineHCID 5324633(2R)-1-Phenoxy-2-propanamineHCID 115971799-(2,3,5-Tri-O-acetyl-beta-D-ribofuranosyl)-6-chloro-2-fluoro-9H-purine

生成物 1

HCID 228772312-fluoro-N-[(R)-1-phenoxy-2-propyl]adenosine収率 28.1%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

9-(2,3,5-Tri- O-acetyl-β-D-ribofuranosyl)-6-chloro-2-fluoro-9H-purine (1.03 g, 2.38 mmol) PCT Publication No. WO 938206, (R)-1-phenoxy-2-propylamine (0.36 g, 2.38 mmol) and triethylamine (0.29 g, 0.28 mmol) in dioxan (20 ml) were stirred at room temperature for 18 h. The reaction mixture was filtered and evaporated to a residue which was purified by flash chromatography. The resultant 2',3',5'-tri- O-acetyl-2-fluoro- N-[(R)-1-phenoxy-2-propyl]adenosine was deprotected using methanolic ammonia to provide the title 2-fluoro- N-[(R)-1-phenoxy-2-propyl]adenosine (0.28 g, 23%)(after column chromatography), mp 148°-150° C.; 1H NMR (DMSO-d6)δ 1.33 (3H, d, -3.59 (1H, m, H-5'a), 3.63-3.71 (1H, m, H-5'b), 3.92-3.99 (2H, m, H-4' and --C--H), 4.10-4.18 (2H, m, H-3' and --C--H), 4.51 (1H, q, H-2'), 4.61 (1H, m, --CH3C H--), 5.06 (1H, t, 5'-OH), 5.22, 5.48 (2H, 2d, 2' and 3'-OH), 5.82 (1H, d, H-1'), 6.89-6.97 (3H, m, Ar--H), 7.25-7.30 (2H, t, Ar--H), 8.39 (1H, s, H-8), 8.49 (1H, d, N--H).

後処理

  1. filtrationThe reaction mixture was filtered
  2. customevaporated to a residue which
  3. customwas purified by flash chromatography

出典と根拠

ORDレコード
ord-1cae8501a66f47d7bdfd5eb71cd00e77
出典データセット
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05672588

反応ノート

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