Potassium Carbonate → (R)-5-[N-(t-Butyloxycarbonyl)-2-aminopropyl]-1,3-benzodioxole-2,2-dicarboxylic acid, diethyl ester

HRID 1524

反応式

HRID 1524 の反応式
[OH:1][C:2]1[CH:3]=[C:4]([C@@H:9](C)[CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[CH:6][C:7]=1[OH:8].[C:20](=O)([O-])[O-].[K+].[K+].Br[C:27](Br)([C:33]([O:35][CH2:36][CH3:37])=[O:34])[C:28]([O:30][CH2:31][CH3:32])=[O:29]>CC(C)=O>[C:14]([O:13][C:12]([NH:11][C@H:10]([CH3:20])[CH2:9][C:4]1[CH:5]=[CH:6][C:7]2[O:8][C:27]([C:33]([O:35][CH2:36][CH3:37])=[O:34])([C:28]([O:30][CH2:31][CH3:32])=[O:29])[O:1][C:2]=2[CH:3]=1)=[O:18])([CH3:15])([CH3:16])[CH3:17]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 69427Propanedioic acid, 2,2-dibromo-, 1,3-diethyl esterHCID 86752190(R)-2-(3,4-Dihydroxyphenyl)propylcarbamic acid, t-butyl ester

生成物 1

HCID 54476420(R)-5-[N-(t-Butyloxycarbonyl)-2-aminopropyl]-1,3-benzodioxole-2,2-dicarboxylic acid, diethyl ester

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

反応条件

温度
60 °C

実験手順

A solution of (R)-2-(3,4-dihydroxyphenyl)propylcarbamic acid, t-butyl ester. (1.07 g, 4 mMol) in acetone (25 ml) containing potassium carbonate (3 equiv, 1.66 g, 12 mMol) was stirred at 60° C. under an argon atmosphere for 1 hour. After cooling to ambient temperature, a solution of diethyl dibromomalonate (1.27 g, 4 mMol) in acetone (7 ml) was added and the reaction was stirred at ambient temperature for 18 hours. The suspension was filtered and the residue was washed with ethyl acetate. The filtrates were combined, evaporated and the residue was partitioned between ethyl acetate (200 ml) and dilute hydrochloric acid (100 ml, pH5). The organic layer was separated, washed with water (2×100 ml) and brine (100 ml), dried (MgSO4) and evaporated. The residue was purified by column chromatography on silica gel eluting with 25% ethyl acetate in n-hexane giving the title compound as an oil;

後処理

  1. temperatureAfter cooling to ambient temperature
  2. stirringthe reaction was stirred at ambient temperature for 18 hours
  3. filtrationThe suspension was filtered
  4. washthe residue was washed with ethyl acetate
  5. customevaporated
  6. customthe residue was partitioned between ethyl acetate (200 ml) and dilute hydrochloric acid (100 ml, pH5)
  7. customThe organic layer was separated
  8. washwashed with water (2×100 ml) and brine (100 ml)
  9. dry with materialdried (MgSO4)
  10. customevaporated
  11. customThe residue was purified by column chromatography on silica gel eluting with 25% ethyl acetate in n-hexane giving the title compound as an oil

出典と根拠

ORDレコード
ord-15507b7830194c87ab4d8306a193e36d
出典データセット
uspto-grants-1998_03
特許番号
US05726165

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