Triethylamine → HCID 54230558, compound

HRID 1793255Notes

Reaction equation

HRID 1793255 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].C(N(CC)CC)C.[F:27][C:28]([F:35])([F:34])[C:29](OCC)=[O:30]>CO>[F:27][C:28]([F:35])([F:34])[C:29]([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:30]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 22881721HCID 22881721, compound

Product 1

HCID 54230558HCID 54230558, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4′-C-Aminomethylthymidine (4) (1.5 mmol) was dissolved in methanol (10 mL) and triethylamine (1.5 mL) at ambient temperature. The solution was then treated with neat ethyl trifluoroacetate (1 mL) and the resulting solution stirred for 18 hours at ambient temperature with exclusion of moisture. The solvents and reagents were then removed under vacuum to give the crude product. Purification by flash column chromatography (9:1 dichloromethane:methanol) afforded the title compound (7) as a white foam (0.37 g, 66%). δH(300 MHz, CD3OD) 8.77(1H, t, br, N3—H), 7.73(1H, s, H-6), 6.24(1H, dd, H-1′), 4.56(1H, dd, H-3′), 3.6(3H, s, H-5′, obs d, 4′-C—CH2), 3.53(1H, d, 4′-C—CH2), 2.35(2H, m, H-2′), 1.81(3H, s, 5-CH3); δC(75.45 MHz, CD3OD), 166.24, 160.08–158.62(q, CF3CO), 152.21, 138.11, 123.01–111.51(q, CF3CO), 111.51, 88.93, 85.69, 72.79, 64.23, 41.70, 40.81, 12.40; ES +ve m/z 368 (M+H)+, 390(M+Na)+; ν cm−1 1684. For an alternative synthesis of this compound see Wang et al, Tetrahedron Letters 1996, 37, 6515–6518.

Workup

  1. customat ambient temperature
  2. customThe solvents and reagents were then removed under vacuum
  3. customto give the crude product
  4. customPurification by flash column chromatography (9:1 dichloromethane:methanol)

Sources & evidence

ORD record
ord-2a2225e84c354943a777719f4cd032d4
Source dataset
uspto-grants-2006_07
Patent number
US07078499B2

Reaction notes

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