HCID 86760969, compound → HCID 86760968, compound

HRID 1820602Notes

Reaction equation

HRID 1820602 reaction equation
[C:1]([CH:6]=[CH:7][CH:8]=[CH:9][C:10]1[C:11](=[O:25])[NH:12][C:13](=[O:24])[N:14]([CH:23]=1)[C@@H:15]1[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[CH2:16]1)([O:3]CC)=[O:2]>[OH-].[Na+]>[C:1]([CH:6]=[CH:7][CH:8]=[CH:9][C:10]1[C:11](=[O:25])[NH:12][C:13](=[O:24])[N:14]([CH:23]=1)[C@@H:15]1[O:22][C@H:19]([CH2:20][OH:21])[C@@H:17]([OH:18])[CH2:16]1)([OH:3])=[O:2]

Participants

3

Reactant 1

HCID 86760969HCID 86760969, compound

Product 1

HCID 86760968HCID 86760968, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
25 °C

Procedure

5-(4-Carbethoxy-1,3-butadienyl)-2′-deoxyuridine (V, from Example 1) (0.449 g, 1.28 mmol) was dissolved in 2N NaOH (3 mL) and stirred at 25° C. After 20 mm, a precipitate was formed and TLC showed that the starting material was completely consumed. The mixture was cooled to 0° C. and acidified to pH 1 with 2N HCl. The resulting off-white solid was filtered off, washed with water and dried in vacuo to give 0.225 g (54%) product.

Workup

  1. customAfter 20 mm, a precipitate was formed
  2. customwas completely consumed
  3. temperatureThe mixture was cooled to 0° C.
  4. filtrationThe resulting off-white solid was filtered off
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-d47ea5aa30ae4f2e900dbb3bde7d8c7a
Source dataset
uspto-grants-2009_10
Patent number
US07605144B2

Reaction notes

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