Hydrochloric Acid → HCID 69322448, compound

HRID 352003Notes

Reaction equation

HRID 352003 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 for 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 a and a 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
  6. additiona mixture of a and a diasteriomers

Sources & evidence

ORD record
ord-e6af519d67fe4ca9ad9496618aad2189
Source dataset
uspto-grants-2004_06
Patent number
US06743902B1

Reaction notes

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