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

HRID 50078ノート

反応式

HRID 50078 の反応式
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

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 178522340HCID 178522340、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

In a three-necked round bottom flask equipped with mechanical stirring and 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 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 minutes, 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 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=7.321 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).

後処理

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

出典と根拠

ORDレコード
ord-bb45daa5037a425ca0c323bdece3390a
出典データセット
uspto-grants-2004_03
特許番号
US06710164B1

反応ノート

読み込み中…