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

HRID 963938Notes

Reaction equation

HRID 963938 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 bottom flask equipped with a mechanical stirrer and a nitrogen inlet was placed methyl bromacetate (7.82 mL, 82.6 mmol) and a suspension of N4 -benzyloxycarbonyl-cytosine (9, 21 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 4N 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 minutes, filtered, cooled to 0° C., and 4N hydrochloric acid (35 mL) was added. The title compound was isolated by filtration, washed with water, recrystallized from methanol (1000 mL) and washed with ether. This afforded 7.70 g (31%) of pure title compound. The mother liquor from 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=7.32Hz, 1H, H-6); 7.39 (s, 5H, Ph); 7.01 (d, J=7.32Hz, 1H, H-5); 5.19 (s, 2H, PhCH2 --); 4.52 (s, 2H).

Workup

  1. customIn a three-necked round bottom flask equipped with a mechanical stirrer and a nitrogen inlet
  2. filtrationfiltered
  3. customevaporated to dryness, in vacuo
  4. additionWater (300 mL) and 4N hydrochloric acid (10 mL) were added
  5. stirringthe mixture was stirred for 15 minutes at 0° C.
  6. filtrationfiltered
  7. washwashed with water (2×75 mL)
  8. additionThe isolated precipitate was treated with water (120 mL), 2N sodium hydroxide (60 mL)
  9. stirringstirred for 30 minutes
  10. filtrationfiltered
  11. addition4N hydrochloric acid (35 mL) was added

Sources & evidence

ORD record
ord-b7db8ca5121b4483b7f04b7aa1f5bdf8
Source dataset
uspto-grants-1998_06
Patent number
US05766855

Reaction notes

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