Hydrochloric Acid → (1S,2S,3R,5S)-3-(7-Chloro-5-(Propylthio)-3H-[1,2,3]Triazolo[4,5-d]Pyrimidin-3-Yl)-5-(2-Hydroxyethoxy)Cyclopentane-1,2-Diol

HRID 589817ノート

反応式

HRID 589817 の反応式
Cl.[NH2:2][C:3]1[C:4]([NH:14][C@H:15]2[C@@H:19]3[O:20]C(C)(C)[O:22][C@@H:18]3[C@@H:17]([O:25][CH2:26][CH2:27][OH:28])[CH2:16]2)=[N:5][C:6]([S:10][CH2:11][CH2:12][CH3:13])=[N:7][C:8]=1[Cl:9].[N:29]([O-])=O.[Na+]>O>[Cl:9][C:8]1[C:3]2[N:2]=[N:29][N:14]([C@@H:15]3[CH2:16][C@H:17]([O:25][CH2:26][CH2:27][OH:28])[C@@H:18]([OH:22])[C@H:19]3[OH:20])[C:4]=2[N:5]=[C:6]([S:10][CH2:11][CH2:12][CH3:13])[N:7]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 102021862-(((3aR,4S,6R,6aS)-6-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanolHCID 23668193Sodium Nitrite

生成物 1

HCID 71609809(1S,2S,3R,5S)-3-(7-Chloro-5-(Propylthio)-3H-[1,2,3]Triazolo[4,5-d]Pyrimidin-3-Yl)-5-(2-Hydroxyethoxy)Cyclopentane-1,2-Diol収率 80%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A flask was charged with water (20 mL) and concentrated hydrochloric acid (35%, 1.5 mL). To this, 2-(((3aR,4S,6R,6aS)-6-((5-amino-6-chloro-2-(propylthio)pyrimidin-4-yl)amino)-2,2-dimethyltetrahydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)oxy)ethanol (5 g) was added and the mixture was stirred for clear solution. To this mixture, aqueous sodium nitrite solution (0.86 g in 5 mL) was slowly added at room temperature over a period of 15 minutes and mixture was stirred for about 30 minutes and completion of reaction was monitored by TLC. The solid obtained is isolated by filtration and washed with water (5 mL) and dried under vacuum to afford the title compound in about 80% yield.

後処理

  1. stirringmixture was stirred for about 30 minutes
  2. customcompletion of reaction
  3. customThe solid obtained
  4. customis isolated by filtration
  5. washwashed with water (5 mL)
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-354ff8d2736741a89d6dbabd8e30e0fc
出典データセット
uspto-grants-2016_01
特許番号
US09233966B2

反応ノート

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