Diethyl Ether → HCID 178510944, compound

HRID 1695093Notes

Reaction equation

HRID 1695093 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:11][CH2:12][CH2:13][NH:14]C(OC(C)(C)C)=O)[NH:8]2)=[C:4]([O:22][CH2:23][C:24]2[CH:37]=[CH:36][C:27]([CH2:28][NH:29][C:30](=[O:35])[C:31]([F:34])([F:33])[F:32])=[CH:26][CH:25]=2)[N:3]=1.FC(F)(F)C(O)=O.C(OCC)C>ClCCl>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[C:7]([CH2:11][CH2:12][CH2:13][NH2:14])[NH:8]2)=[C:4]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([CH2:28][NH:29][C:30](=[O:35])[C:31]([F:32])([F:34])[F:33])=[CH:36][CH:37]=2)[N:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 178453369N-[4-(2-Amino-8-(3-(tert-butoxycarbonylamino)-propyl)-9H-purin-6-yloxymethyl)-benzyl]-2,2,2-trifluoro-acetamide

Product 1

HCID 178510944HCID 178510944, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The tert-butoxycarbonyl derivative 11 (Example 23, 100 mg, 0.19 mmol) is suspended in 10 mL dichloromethane, and 2 mL trifluoroacetic acid are added. The mixture is stirred at room temperature for 30 min and poured into 70 mL of diethyl ether. The precipitate is collected by filtration and purified by flash column chromatography (CH2Cl2/MeOH 5:1) yielding 74 mg (0.17 mmol, 92%) of the title compound. MS (ESI) m/z 424.1 [M+H]+.

Workup

  1. filtrationThe precipitate is collected by filtration
  2. custompurified by flash column chromatography (CH2Cl2/MeOH 5:1)

Sources & evidence

ORD record
ord-ed13f9a25ae144c8878924616a09a422
Source dataset
uspto-grants-2012_04
Patent number
US08163479B2

Reaction notes

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