Cyclopropylamine → HCID 12012064, 화합물

HRID 2118089노트

반응식

HRID 2118089 반응식
[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

참가 물질

4

반응물 2

HCID 69828CyclopropylamineHCID 11749200HCID 11749200, 화합물

생성물 1

HCID 12012064HCID 12012064, 화합물수율 97.6%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d44eb5b3810a48d28b9894ca497e6b92
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442813B2

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