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

HRID 1247375노트

반응식

HRID 1247375 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dac827e433f248cba366bcd93b71ed67
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129238B2

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