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

HRID 744167노트

반응식

HRID 744167 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-794e0b8755f44ed58195358b0017c76e
출처 데이터셋
uspto-grants-1996_09
특허 번호
US05559101

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