Diisopropylethylamine → HCID 86589980, compound

HRID 1793254Notes

Reaction equation

HRID 1793254 reaction equation
[NH2:1][CH2:2][C@:3]1([CH2:18][OH:19])[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:17].[F:20][C:21]([F:30])([F:29])[C:22]([NH:24][CH2:25][C:26](O)=[O:27])=[O:23].C(N(C(C)C)CC)(C)C>CN(C)C=O>[F:20][C:21]([F:30])([F:29])[C:22]([NH:24][CH2:25][C:26]([NH:1][CH2:2][C@:3]1([CH2:18][OH:19])[O:7][C@@H:6]([N:8]2[CH:16]=[C:14]([CH3:15])[C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:17])=[O:27])=[O:23]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 136227N-(trifluoroacetyl)aminoacetic acidHCID 22881721HCID 22881721, compound

Product 1

HCID 86589980HCID 86589980, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4′-C-Aminomethylthymidine (4) (0.14 mmol) was dissolved in anhydrous N,N-dimethylformamide (1 mL). N-Trifluoroacetylglycine (0.036 g, 0.21 mmol) and O-(N-succimidyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate [TSTU] (0.085, 0.28 mmol) were then added and the solution stirred at ambient temperature. Diisopropylethylamine (0.036 g, 0.28 mmol, 0.05 mL) was then added dropwise to the solution with stirring. After 12 hours the solvent was removed under vacuum and the residue redissolved in dichloromethane:methanol (9:1). Applied solution directly to a silica gel column and eluted with dichloromethane:methanol (9:1). Fractions containing the desired material were pooled and the solvent removed under vacuum to give the title compound (5) as a clear, glassy material (0.28 g, 28% from crude 4). δH(300 MHz, CD3OD) 7.91(1H, s, H-6), 6.27(1H, dd, H-1′), 4.49(1H, dd, H-3′), 3.74(2H, s, glycyl CH2), 3.52(1H, d, H-5′), 3.51(2H, s, 4′-C—CH2), 3.43(1H, d, H-5′), 2.32(2H, m, H-2′), 1.68(3H, s, 5-CH3); ES +ve m/z 425(M+H)+, 442(M+H2O)+, 447(M+Na)+.

Workup

  1. stirringwith stirring
  2. customAfter 12 hours the solvent was removed under vacuum
  3. dissolutionthe residue redissolved in dichloromethane:methanol (9:1)
  4. washApplied solution directly to a silica gel column and eluted with dichloromethane:methanol (9:1)
  5. additionFractions containing the desired material
  6. customthe solvent removed under vacuum

Sources & evidence

ORD record
ord-4786a30f4102434ba01e0ca25365f301
Source dataset
uspto-grants-2006_07
Patent number
US07078499B2

Reaction notes

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