Isobutylamine → (RS)-(2,6-difluoro-4-isobutylcarbamoyl-phenyl)-ethoxy-acetic acid ethyl ester

HRID 1247375ノート

反応式

HRID 1247375 の反応式
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([O:15][CH:16]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[C:17]1[C:25]([F:26])=[CH:24][C:20]([C:21]([OH:23])=O)=[CH:19][C:18]=1[F:27])[CH3:14].[CH2:33]([NH2:37])[CH:34]([CH3:36])[CH3:35].CCOC(C)=O>C1COCC1>[CH2:31]([O:30][C:28](=[O:29])[CH:16]([C:17]1[C:18]([F:27])=[CH:19][C:20]([C:21](=[O:23])[NH:37][CH2:33][CH:34]([CH3:36])[CH3:35])=[CH:24][C:25]=1[F:26])[O:15][CH2:13][CH3:14])[CH3:32]

参加物

6

反応物 4

HCID 6558IsobutylamineHCID 8857Ethyl AcetateHCID 682631,1'-CarbonyldiimidazoleHCID 21904951(RS)-4-(ethoxy-ethoxycarbonyl-methyl)-3,5-difluoro-benzoic acid

生成物 1

HCID 69291808(RS)-(2,6-difluoro-4-isobutylcarbamoyl-phenyl)-ethoxy-acetic acid ethyl ester収率 67.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

1,1′-Carbonyldiimidazole (88 mg) was dissolved in THF (1 ml) and a solution of (RS)-4-(ethoxy-ethoxycarbonyl-methyl)-3,5-difluoro-benzoic acid (156 mg) in THF (1 ml) was added. After 30 min stirring at rt isobutylamine (41 mg) was added and the mixture was stirred 3 h. AcOEt (20 ml) was added and the solution was washed with 1 N HCl (20 ml). The aqueous layer was extracted with two more portions AcOEt (20 ml), the the combined organic layers were dried (Na2SO4) and the solvent was evaporated. CC (Hept/AcOET 3:1) afforded 125 mg (67%) of (RS)-(2,6-difluoro-4-isobutylcarbamoyl-phenyl)-ethoxy-acetic acid ethyl ester. White solid.

後処理

  1. additionwas added
  2. washthe solution was washed with 1 N HCl (20 ml)
  3. extractionThe aqueous layer was extracted with two more portions AcOEt (20 ml)
  4. dry with materialthe the combined organic layers were dried (Na2SO4)
  5. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-dac827e433f248cba366bcd93b71ed67
出典データセット
uspto-grants-2006_10
特許番号
US07129238B2

反応ノート

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