Sodium Hydroxide → (+)-5-Methoxycarbonyl-4-methoxymethyl-1,2,3,6-tetrahydro-2-oxo-6 (s)-(3,4-difluorophenyl)-1-[(2-carboxyethylamino)-carbonyl]pyrimidine

HRID 1840325ノート

反応式

HRID 1840325 の反応式
[CH3:1][O:2][C:3]([C:5]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=2)[N:9]([C:19]([NH:21][CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[O:20])[C:8](=[O:29])[NH:7][C:6]=1[CH2:30][O:31][CH3:32])=[O:4].[OH-].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[C@H:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([F:18])[CH:12]=2)[N:9]([C:19]([NH:21][CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[O:20])[C:8](=[O:29])[NH:7][C:6]=1[CH2:30][O:31][CH3:32])=[O:4]

参加物

4

反応物 2

HCID 14798Sodium HydroxideHCID 60101878(+)-5-Methoxycarbonyl-4-methyoxymethyl-1, 2,3,6-tetrahydro-2-oxo-6(S)-(3,4-difluorophenyl)-1-[(2-ethoxycarbonylethylamino)carbonyl]pyrimidine

生成物 1

HCID 59965090(+)-5-Methoxycarbonyl-4-methoxymethyl-1,2,3,6-tetrahydro-2-oxo-6 (s)-(3,4-difluorophenyl)-1-[(2-carboxyethylamino)-carbonyl]pyrimidine

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

(+)-5-Methoxycarbonyl-4-methyoxymethyl-1,2,3,6-tetrahydro-2-oxo-6(S)-(3,4-difluorophenyl)-1-[(2-ethoxycarbonylethylamino)carbonyl]pyrimidine (168 mg, 0.37 mmol) was dissolved in 5 mL of methanol. A 2.0M solution of aqueous sodium hydroxide (400 mL, 0.80 mmol) was added dropwise. The mixture was stirred at ambient temperature for 4.5 hours, then concentrated in vacuo. The resulting residue was partioned between ethyl acetate and 2.0M aqueous hydrochloric acid. The phases were separated and the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were then washed with brine. The organic phase was then dried over sodium sulfate, filtered, and the filtrate was then evaporated to dryness. The residue was reconcentrated from diethyl ether. The resulting white foamy solid was purified by “flash” chromatography (5.02, 98:2:0.2 of dichloromethane:methanol:glacial acetic acid). The product fractions were evaporated to dryness and the residue was reconcentrated from diethyl ether to give the title compound as a white foamy solid.

後処理

  1. concentrationconcentrated in vacuo
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted twice with ethyl acetate
  4. washThe combined organic phases were then washed with brine
  5. dry with materialThe organic phase was then dried over sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate was then evaporated to dryness
  8. customThe resulting white foamy solid was purified by “flash” chromatography (5.02, 98:2:0.2 of dichloromethane:methanol:glacial acetic acid)
  9. customThe product fractions were evaporated to dryness

出典と根拠

ORDレコード
ord-305dae6b63d54bc39d81418cd66cc7fc
出典データセット
uspto-grants-2004_01
特許番号
US06680323B2

反応ノート

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