Ethyl Acetate → 3'-Deoxy-5'-O-(4-methoxytrityl)-3'-(iodomethyl)-2'-O-(2-methoxyethyl)-5-methyluridine

HRID 1836220Notes

Reaction equation

HRID 1836220 reaction equation
[I:1][CH2:2][C@@H:3]1[C@@H:7]([CH2:8][OH:9])[O:6][C@@H:5]([N:10]2[CH:17]=[C:16]([CH3:18])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[C@@H:4]1[O:19][CH2:20][CH2:21][O:22][CH3:23].C(N([CH:30]([CH3:32])[CH3:31])CC)(C)C.[CH2:33]([C:42](Cl)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:34]1C=CC(OC)=C[CH:35]=1.[C:56](OCC)(=[O:58])C>C1COCC1>[CH3:56][O:58][C:31]1[CH:30]=[CH:32][C:33]([C:42]([O:9][CH2:8][C@H:7]2[O:6][C@@H:5]([N:10]3[CH:17]=[C:16]([CH3:18])[C:14](=[O:15])[NH:13][C:11]3=[O:12])[C@H:4]([O:19][CH2:20][CH2:21][O:22][CH3:23])[C@@H:3]2[CH2:2][I:1])([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)=[CH:34][CH:35]=1

Participants

6

Reactant 4

HCID 8857Ethyl Acetate2×HCID 81531DiisopropylethylamineHCID 14836583p-Anisyldiphenylmethyl chlorideHCID 235183313'-Deoxy-3'-(iodomethyl)-2'-O-(2-methoxyethyl)-5-methyluridine

Product 1

HCID 235183323'-Deoxy-5'-O-(4-methoxytrityl)-3'-(iodomethyl)-2'-O-(2-methoxyethyl)-5-methyluridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3′-deoxy-3′-(iodomethyl)-2′-O-(2-methoxyethyl)-5-methyluridine (472 mg, 1.1 mmol), diisopropylethylamine (0.79 mL, 0.586 g, 4.5 mmol), and p-anisyl chlorodiphenyl methane (4′-methoxytrityl chloride, MMT-C1) (1.32 g, 4.27 mmol) in 6 mL of ethyl acetate and 4 mL of THF was stirred at rt for 48 h. The reaction mixture was diluted with ethyl acetate and washed with water, followed by brine. The organic phase was dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography on a silica gel column. Gradient elution with 3:1, 2:1, 1:1, and then 1:3 hexanes-EtOAc provided 690 mg of the title compound as a white foam.

Workup

  1. washwashed with water
  2. dry with materialThe organic phase was dried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography on a silica gel column
  5. washGradient elution with 3:1, 2:1, 1:1

Sources & evidence

ORD record
ord-66a89387fbaf48649d55c706f286a944
Source dataset
uspto-grants-2004_08
Patent number
US06777395B2

Reaction notes

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