Sodium Hydroxide → HCID 13647255, compound

HRID 1732079Notes

Reaction equation

HRID 1732079 reaction equation
[F:1][C@H:2]1[C@H:6]([O:7]C(=O)C2C=CC=CC=2)[C@@H:5]([CH2:16][O:17]C(=O)C2C=CC=CC=2)[O:4][C@H:3]1[N:26]1[CH:33]=[C:32]([I:34])[C:30](=[O:31])[NH:29][C:27]1=[O:28].[OH-].[Na+]>CO.O>[F:1][C@H:2]1[C@H:6]([OH:7])[C@@H:5]([CH2:16][OH:17])[O:4][C@@H:3]1[N:26]1[CH:33]=[C:32]([I:34])[C:30](=[O:31])[NH:29][C:27]1=[O:28]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 1396364697614-45-4

Product 1

HCID 13647255HCID 13647255, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

A slurry of 1-(2-deoxy-2-fluoro-3,5-di-O-benzoyl-β-D-arabinofuranosyl)-5-iodouracil (4.7 g, 0.0081 mole) from Procedure 6 in 60 mL 50% MeOH/H2O is stirred at 25° C. maintained at pH 10.5 with 3N NaOH until complete dissolution of solid occurs. Progress of the hydrolysis is followed by HPLC (mobile phase=70% H2O/30% MeOH, flow rate=1 mL/min., wave length=282 nm UV detection, column=Whatman 10 ODS-3 reverse-phase 25 cm., injection volume=20 μl at ~0.5 mg/l concentration, α-IX=6.86 min., β-IX=7.98 min., and 5-iodouracil=4.5 min.). When the reaction is complete (16 hr.), 25 mL of water is added and the mixture is concentrated to approximately 30 mL. The clear aqueous concentrate is adjusted to pH 6.5 to 7.0 with 3N HCl. A solid forms, the mixture is stirred at 25° C. for 2 hrs., and at 0° to 5° C. for 5 hrs. The solid is collected by filtration, washed with 30 mL cold H2O and dried at 50° C./5 mm. The yield of product is 2.7 g (90%), mp 223°-226° [360 MHz NMR (CD3OD) 8.28, d, 1H; 6.16, dd, 1H; 5.04, m, 1H; 4.32, m, 1H; 3.95-3.7, m, 3H. Elemental analysis calculated: %C 29.05, %H 2.71, %N 7.53; Found: %C 28.86, %H 2.64, %N 7.50; IR (KBr) NH, OH 3400, 3200 cm-1 ; CO--NH--CO 1725, 1655 cm-1, C--O 1050 cm-1.]

Workup

  1. concentrationProgress of the hydrolysis is followed by HPLC (mobile phase=70% H2O/30% MeOH, flow rate=1 mL/min., wave length=282 nm UV detection, column=Whatman 10 ODS-3 reverse-phase 25 cm., injection volume=20 μl at ~0.5 mg/l concentration, α-IX=6.86 min., β-IX=7.98 min., and 5-iodouracil=4.5 min.)
  2. custom(16 hr.), 25 mL of water
  3. additionis added
  4. concentrationthe mixture is concentrated to approximately 30 mL
  5. concentrationThe clear aqueous concentrate
  6. wait, and at 0° to 5° C. for 5 hrs
  7. filtrationThe solid is collected by filtration
  8. washwashed with 30 mL cold H2O
  9. customdried at 50° C./5 mm

Sources & evidence

ORD record
ord-1d9321df70c0452f9c46c8f61332bf95
Source dataset
uspto-grants-1986_11
Patent number
US04625020

Reaction notes

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