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Dimethylformamide → 3-(2-Carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indan-2-ylacetic acid

HRID 650422
ノート
印刷プレビュー

反応式

HRID 650422 の反応式
[C:1]([CH2:8][O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[CH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH2:28][CH2:29][CH3:30])[CH:25]=2)[CH:20]([C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)[CH:19]1[CH2:40]C#N)([O:3]C(C)(C)C)=[O:2].C(CC1C(C2C=CC([O:61]C)=CC=2O)C2C(=CC=C(OCCC)C=2)C1C1C=CC2OCOC=2C=1)#N.[H-].[Na+].C(OC(=O)CBr)CCC.CN([CH:91]=[O:92])C>>[C:1]([CH2:8][O:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=1[CH:18]1[C:26]2[C:21](=[CH:22][CH:23]=[C:24]([O:27][CH2:28][CH2:29][CH3:30])[CH:25]=2)[CH:20]([C:31]2[CH:36]=[CH:35][C:34]3[O:37][CH2:38][O:39][C:33]=3[CH:32]=2)[CH:19]1[CH2:40][C:91]([OH:92])=[O:61])([OH:3])=[O:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 5

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 87883Butyl bromoacetateHCID 867521292-Cyanomethyl-3-(2-hydroxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indaneHCID 1317204703-(2-Carbo-t-butoxymethoxy-4-methoxyphenyl)-2-cyanomethyl-1-(3,4-methylenedioxyphenyl)-5-propoxyindane

生成物 1

HCID 10166371
3-(2-Carboxymethoxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indan-2-ylacetic acid
収率 79%

反応条件

温度
0 °C

実験手順

1RS,2RS,3RS)-3-(2-Carbo-t-butoxymethoxy-4-methoxyphenyl)-2-cyanomethyl-1-(3,4methylenedioxyphenyl)-5-(prop-1-yloxy)indane. To a solution of 1RS,2RS,3RS)-2-cyanomethyl-3-(2-hydroxy-4-methoxyphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane (250 mg, 0.55 mmol) in DMF (4 ml) stirred at 0° C. under argon added NaH (21 mg of 80% oil dispersion, 0.7 mmol). The mixture stirred at 0° C. for 15 min then t -butylbromoacetate (107 mg, 0.55 mmol) was added. The cooling bath was removed and the mixture was stirred for 3 h at room temperature then partitioned between EtOAc and 3N HCl. The organic extract was washed with H2O, saturated NaHCO3 solution, H2O, then brine, dried (Na2SO4) and solvent removed in vacuo. The residue was purified by flash chromatography on silica gel, (eluent 25-50% Et2O/hexanes) to afford the title compound as an oil (247 mg, 79%).

後処理

  1. additionwas added
  2. customThe cooling bath was removed
  3. stirringthe mixture was stirred for 3 h at room temperature
  4. customthen partitioned between EtOAc and 3N HCl
  5. extractionThe organic extract
  6. washwas washed with H2O, saturated NaHCO3 solution, H2O
  7. dry with materialbrine, dried (Na2SO4) and solvent
  8. customremoved in vacuo
  9. customThe residue was purified by flash chromatography on silica gel, (eluent 25-50% Et2O/hexanes)

出典と根拠

ORDレコード
ord-5ff1755585c44a8686644585fe28b04a
出典データセット
uspto-grants-2001_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06271399B1

反応ノート

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