Cyclopropylamine → HCID 12012064、化合物

HRID 2118089ノート

反応式

HRID 2118089 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][O:14][C@@H:13]([CH2:16][O:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:12]2)=[C:4](Cl)[N:3]=1.[CH:27]1([NH2:30])[CH2:29][CH2:28]1>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][O:14][C@@H:13]([CH2:16][O:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:12]2)=[C:4]([NH:30][CH:27]2[CH2:29][CH2:28]2)[N:3]=1

参加物

4

反応物 2

HCID 69828CyclopropylamineHCID 11749200HCID 11749200、化合物

生成物 1

HCID 12012064HCID 12012064、化合物収率 97.6%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

Benzoic acid 4(R)-(2-amino-6-chloro-purin-9-yl)-[1,3]dioxolan-2(R)-ylmethyl ester (1266 g, cis/trans:1.9/1), ethanol (20 L), and cyclopropylamine (643 g) were refluxed for 16 hours. The reaction mixture was cooled and concentrated to a residue. The residue was dissolved in dichloromethane (3.6 L) and agitated with an aqueous solution of sodium bicarbonate for 30 minutes. After settling the organic layer was separated and the aqueous was back-extracted with dichloromethane (2×750 mL). The combined organic layers were concentrated to give a yellow-brown foam (1304 g) of material (9) which is suitable for reaction in the subsequent deprotection step in NH3/MeOH.

後処理

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated to a residue
  3. dissolutionThe residue was dissolved in dichloromethane (3.6 L)
  4. customwas separated
  5. extractionthe aqueous was back-extracted with dichloromethane (2×750 mL)
  6. concentrationThe combined organic layers were concentrated

出典と根拠

ORDレコード
ord-d44eb5b3810a48d28b9894ca497e6b92
出典データセット
uspto-grants-2008_10
特許番号
US07442813B2

反応ノート

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