Hydrochloric Acid → HCID 69322448, compound

HRID 636281Notes

Reaction equation

HRID 636281 reaction equation
Br[C@@:2]1([N:28]2[CH2:36][C:34]([CH:37]([O:44][CH3:45])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([CH3:35])[C:32](=[O:33])[NH:31][C:29]2=[O:30])[O:18][C@H:6]([CH:7]([CH:9]([O:16][CH3:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:8])[C@@:4]([CH:19]([O:26][CH3:27])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([OH:5])[CH2:3]1.[O-:46][CH2:47][CH3:48].[Na+].Cl>C(O)C>[CH2:47]([O:46][C@@:2]1([N:28]2[CH2:36][C:34]([CH:37]([O:44][CH3:45])[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)([CH3:35])[C:32](=[O:33])[NH:31][C:29]2=[O:30])[O:18][C@H:6]([CH:7]([CH:9]([O:16][CH3:17])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:8])[C@@:4]([CH:19]([O:26][CH3:27])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([OH:5])[CH2:3]1)[CH3:48]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 69910680HCID 69910680, compound

Product 1

HCID 69322448HCID 69322448, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1′-bromo-3′, 5′, 5-tris(methoxybenzyl)thymidine in ethanol is added to a stirred solution of sodium ethoxide in ethanol at −10° C. The resulting reaction mixture is stirred at room temperature fro 1 h, neutralized with dilute hydrochloric acid. Ethanol is evaporated and the remaining mixture extracted with ethyl acetate. The crude is purified by chromatography to give a mixture of α and β diasteriomers.

Workup

  1. customThe resulting reaction mixture
  2. customEthanol is evaporated
  3. extractionthe remaining mixture extracted with ethyl acetate
  4. customThe crude is purified by chromatography
  5. customto give

Sources & evidence

ORD record
ord-39a2ecba4a3e4f249d0d070daa449d37
Source dataset
uspto-grants-2001_02
Patent number
US06191266B1

Reaction notes

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