Hydrochloric Acid → HCID 58739076, compound

HRID 720278Notes

Reaction equation

HRID 720278 reaction equation
C([O:3][C:4]([C:6]1[N:7]=[C:8]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][S:17]2(=[O:23])=[O:22])[N:9]([CH3:15])[C:10](=[O:14])[C:11]=1[O:12][CH3:13])=[O:5])C.[OH-].[Na+].Cl>C(O)C>[O:23]=[S:17]1(=[O:22])[CH2:18][CH2:19][CH2:20][CH2:21][N:16]1[C:8]1[N:9]([CH3:15])[C:10](=[O:14])[C:11]([O:12][CH3:13])=[C:6]([C:4]([OH:5])=[O:3])[N:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58739069HCID 58739069, compound

Product 1

HCID 58739076HCID 58739076, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-(1,1-dioxo-1λ6-[1,2]thiazinan-2-yl)-5-methoxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (0.180 g, 0.52 mmol) in 90% ethanol (10 ml) was treated at 22° C. 1 N with sodium hydroxide (1 ml) and the resulting mixture was stirred for 30 min. Then 1 N hydrochloric acid (2 ml) was added and the ethanol was evaporated under reduced pressure. The residue was dissolved in ethyl acetate, washed with brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent and recrystallization of the solid residue from ethyl acetate gave 0.133 g (81% yield) of the title acid as a white crystals; mp 180–181° C. 1HNMR 400 MHz (DMSO-d6) δ (ppm): 1.55–1.6 (1H, m, CH), 2.0–2.25 (3H, m, CH2 and CH), 3.43 (2H, m, CH2), 3.44 (3H, s, NCH3), 3.75 (2H, m, CH2), 3.83 (3H, s, OCH3). Anal. Calcd for C11H15N3O6S: C, 41.64; H, 4.76; N, 13.24. Found: C, 41.84; H, 4.96; N, 12.88.

Workup

  1. customthe ethanol was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent and recrystallization of the solid residue from ethyl acetate

Sources & evidence

ORD record
ord-ff58c5bfa79b4a06bef6e8222ea57a45
Source dataset
uspto-grants-2006_11
Patent number
US07135467B2

Reaction notes

Loading…