Potassium Carbonate → 2-(4-(((Benzyloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acid

HRID 1976797Notes

Reaction equation

HRID 1976797 reaction equation
Br[CH2:2][C:3]([O:5]C)=[O:4].[CH2:7]([O:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][NH:21][C:20](=[O:24])[N:19]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:7]([O:14][C:15]([NH:17][C:18]1[CH:23]=[CH:22][N:21]([CH2:2][C:3]([OH:5])=[O:4])[C:20](=[O:24])[N:19]=1)=[O:16])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 178522340HCID 178522340, compound

Product 1

HCID 7254702-(4-(((Benzyloxy)carbonyl)amino)-2-oxopyrimidin-1(2H)-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

In a three necked round bottomed flask equipped with mechanical stirring and nitrogen coverage was placed methyl bromacetate (7.82 ml;82.6 mmol) and a suspension of N4-benzyloxycarbonyl-cytosine (9, 21.0 g; 82.6 mmol) and potassium carbonate (11.4 g; 82.6 mmol) in dry DMF (900 ml). The mixture was stirred vigorously overnight, filtered, and evaporated to dryness, in vacuo. Water (300 ml) and 4 N hydrochloric acid (10 ml) were added, the mixture was stirred for 15 minutes at 0° C., filtered, and washed with water (2×75 ml). The isolated precipitate was treated with water (120 ml), 2N sodium hydroxide (60 ml), stirred for 30 min, filtered, cooled to 0° C., and 4 N hydrochloric acid (35 ml) was added. The title compound was isolated by filtration, washed thoroughly with water, recrystallized from methanol (1000 ml) and washed thoroughly with ether. This afforded 7.70 g (31%) of pure compound. The mother liquor from the recrystallization was reduced to a volume of 200 ml and cooled to 0° C. This afforded an additional 2.30 g of a material that was pure by tlc but had a reddish color. M.p. 266-274° C. Anal. for C14H13N3O5. Found(calc.); C: 55.41(55.45); H: 4.23(4.32); N: 14.04(13.86). 1H-NMR (90 MHz; DMSO-d6): 8.02 ppm (d,J=7.32 Hz,1H,H-6); 7.39 (s,5H, Ph) 7.01 (d,J=7.32 Hz,1H, H-5); 5.19 (s,2H,PhCH2—); 4.52 (s,2H).

Workup

  1. customIn a three necked round bottomed flask equipped
  2. stirringThe mixture was stirred vigorously overnight
  3. filtrationfiltered
  4. customevaporated to dryness, in vacuo
  5. additionWater (300 ml) and 4 N hydrochloric acid (10 ml) were added
  6. stirringthe mixture was stirred for 15 minutes at 0° C.
  7. filtrationfiltered
  8. washwashed with water (2×75 ml)
  9. additionThe isolated precipitate was treated with water (120 ml), 2N sodium hydroxide (60 ml)
  10. stirringstirred for 30 min
  11. filtrationfiltered
  12. addition4 N hydrochloric acid (35 ml) was added

Sources & evidence

ORD record
ord-97ffbd45b8c24755b3219ab3880eefb6
Source dataset
uspto-grants-2001_05
Patent number
US06228982B1

Reaction notes

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