HCID 20026552, compound → HCID 14536311, compound

HRID 1723042Notes

Reaction equation

HRID 1723042 reaction equation
C([O:9][CH2:10][C:11]1([CH2:23][O:24]C(=O)C2C=CC=CC=2)[CH2:13][CH:12]1[CH2:14][N:15]1[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]1=[O:17])(=O)C1C=CC=CC=1>Cl>[OH:24][CH2:23][C:11]1([CH2:10][OH:9])[CH2:13][CH:12]1[CH2:14][N:15]1[CH:22]=[CH:21][C:19](=[O:20])[NH:18][C:16]1=[O:17]

Participants

3

Reactant 1

HCID 20026552HCID 20026552, compound

Product 1

HCID 14536311HCID 14536311, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A suspension of 3.62 mmoles of 1-[2,2-bis(benzoyloxymethyl)-1-cyclopropylmethyl]uracil in 178 ml of 2.5N HCl is stirred at 100° for about 5 hours. The reaction mixture is concentrated to a residual semi-solid which is triturated with three 20 ml portions of Et2O and dried, and the residue is dissolved in 5 ml of water and neutralized (pH 7) with 2N NaOH. The solid separates and is removed and dried, and the filtrate is concentrated to dryness. The solids are then combined, dissolved in a small amount of CHCl3 -MeOH (1:1) and put on five 2000 micron preparative TLC plates which are developed in CMW (70:30:3). The product bands (Rf 0.3) are eluted with CHCl3 -MeOH (3:2) and when concentrated yield the titled product.

Workup

  1. concentrationThe reaction mixture is concentrated to a residual semi-solid which
  2. customis triturated with three 20 ml portions of Et2O
  3. customdried
  4. dissolutionthe residue is dissolved in 5 ml of water
  5. customThe solid separates and is removed
  6. customdried
  7. concentrationthe filtrate is concentrated to dryness
  8. dissolutiondissolved in a small amount of CHCl3 -MeOH (1:1)
  9. washThe product bands (Rf 0.3) are eluted with CHCl3 -MeOH (3:2) and when
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-3d9e8f34e54e4a10a5deeeb61377d154
Source dataset
uspto-grants-1989_08
Patent number
US04859680

Reaction notes

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