Triethylamine → HCID 10133917, compound

HRID 1270256Notes

Reaction equation

HRID 1270256 reaction equation
C(N(CC)CC)C.[Si]([O:25][CH2:26][C@H:27]1[O:31][C@@H:30]([N:32]2[CH:39]=[C:38]([CH3:40])[C:36](=[O:37])[NH:35][C:33]2=[O:34])[C@H:29]([O:41][CH2:42][CH2:43][O:44][N:45]([CH2:48][CH3:49])[CH2:46][CH3:47])[C@@H:28]1[OH:50])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1>[CH2:48]([N:45]([CH2:46][CH3:47])[O:44][CH2:43][CH2:42][O:41][C@@H:29]1[C@H:28]([OH:50])[C@@H:27]([CH2:26][OH:25])[O:31][C@H:30]1[N:32]1[CH:39]=[C:38]([CH3:40])[C:36](=[O:37])[NH:35][C:33]1=[O:34])[CH3:49]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 23518340HCID 23518340, compound

Product 1

HCID 10133917HCID 10133917, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of triethlyamine trihydrogenfluoride (4.39 mL, 26.81 mmol) and triethylamine (1.87 mL, 13.41 mmol) in THF (53.6 mL) was added to 5′-O-tert-butyldiphenylsilyl-2′-O-[2-(N,N-diethylaminooxy)ethyl]-5-methyluridine (3.28 g, 5.36 mmol). The reaction mixture was stirred at room temperature for 18 h. Solvent was removed in vacuo. The residue was placed on a silica gel column and eluted with CH2Cl2/MeOH/NEt3, 89:10:1, to yield the title compound (1.49 g). 1H NMR (DMSO-d6): δ 0.97 (t, 6H, J=7.2 Hz), 1.75 (s, 3H), 2.58 (q, 4H, J=7.2 Hz), 3.55 (m, 4H), 3.66 (m, 2H), 3.83 (bs, 1H), 3.95 (t, 1H, J=5.6 Hz), 4.11 (q, 1H, J=4.8 Hz and 5.6 Hz), 5.05 (d, 1H, J=5.6 Hz), 5.87 (d, 1H, J=6.0 Hz), 7.75 (s, 1H), 11.31 (s, 1H); 13C NMR (CDCl3): δ 11.75, 12.27, 52.24, 61.31, 68.86, 70.19, 72.25, 81.49, 85.10, 90.29, 110.60, 137.79, 150.57, 164.37; HRMS (FAB) Calcd for C16H28N3O7⊕ 374.1927, found 374.1919.

Workup

  1. customSolvent was removed in vacuo
  2. washeluted with CH2Cl2/MeOH/NEt3, 89:10:1

Sources & evidence

ORD record
ord-367917b92d66438caf59ea660cc18b2e
Source dataset
uspto-grants-2007_04
Patent number
US07202224B2

Reaction notes

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