Acetic Acid → 9-((2S,3S,4R,5S)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one

HRID 744167ノート

反応式

HRID 744167 の反応式
C([O:9][C@H:10]1[C@@H:14]([O:15]C(=O)C2C=CC=CC=2)[C@H:13]([CH2:24][O:25]C(=O)C2C=CC=CC=2)[O:12][C@@H:11]1[N:34]1[CH:42]=[N:41][C:40]2[C:35]1=[N:36][CH:37]=[N:38][C:39]=2Cl)(=O)C1C=CC=CC=1.SC([OH:47])C.C[O-].[Na+].C(O)(=O)C>CO>[C@H:11]1([N:34]2[CH:42]=[N:41][C:40]3[C:39](=[O:47])[NH:38][CH:37]=[N:36][C:35]2=3)[O:12][C@@H:13]([CH2:24][OH:25])[C@H:14]([OH:15])[C@@H:10]1[OH:9]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 4713212Mercapto-ethanolHCID 10942334Sodium MethoxideHCID 86749850[(2S,3S,4S,5S)-3,4-dibenzoyloxy-5-(6-chloropurin-9-yl)oxolan-2-yl]methyl benzoate

生成物 1

HCID 1355222619-((2S,3S,4R,5S)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one収率 1,359.3%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 9 (1.05 g, 1.70 mmol), mercaptoethanol (0.48 ml, 6.9 mmol), and NaOMe in MeOH (100 ml) was refluxed for four hours. The reaction mixture was cooled, neutralized with glacial acetic acid and evaporated to dryness. The solid obtained was washed with CHCl3 and the residue was crystallized from EtOH to give pure 11 (6.198 g, 47%) as white crystals: m.p. 212°-213° C. (dec).

後処理

  1. temperaturewas refluxed for four hours
  2. temperatureThe reaction mixture was cooled
  3. customevaporated to dryness
  4. customThe solid obtained
  5. washwas washed with CHCl3
  6. customthe residue was crystallized from EtOH

出典と根拠

ORDレコード
ord-794e0b8755f44ed58195358b0017c76e
出典データセット
uspto-grants-1996_09
特許番号
US05559101

反応ノート

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