Sodium hydride → methyl (E)-2-benzoylamino-3-(2,4-dibenzyloxyphenyl)acrylate

HRID 322932

반응식

HRID 322932 반응식
[C:1]([NH:9][CH:10](P(OC)(OC)=O)[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:23]([O:30][C:31]1[CH:38]=[C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[CH:36]=[CH:35][C:32]=1[CH:33]=O)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>O1CCCC1>[C:1]([NH:9]/[C:10](=[CH:33]/[C:32]1[CH:35]=[CH:36][C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:38][C:31]=1[O:30][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)/[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[C:1]([NH:9]/[C:10](=[CH:33]\[C:32]1[CH:35]=[CH:36][C:37]([O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[CH:38][C:31]=1[O:30][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)/[C:11]([O:13][CH3:14])=[O:12])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 18090802,4-Bis(benzyloxy)benzaldehydeHCID 14104867Methyl 2-benzamido-2-(dimethoxyphosphoryl)acetate

생성물 2

HCID 22010495methyl (E)-2-benzoylamino-3-(2,4-dibenzyloxyphenyl)acrylateHCID 70223822methyl (Z)-2-benzoylamino-3-(2,4-dibenzyloxyphenyl)acrylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A stirred solution of methyl benzoylamino(dimethoxyphosphoryl)acetate (4.25 g) in dry tetrahydrofuran (30 mL) is treated with sodium hydride (0.66 g, 60% dispersion in mineral oil) under nitrogen. After stirring for 15 minutes a solution of 2,4-dibenzyloxybenzaldehyde (4.74 g) in dry tetrahydrofuran (15 mL) is added dropwise. The reaction mixture is stirred at room temperature for 18 hours, evaporated and the residue partitioned between ethyl acetate (100 mL) and water (75 mL). The organic phase is washed with brine (50 mL), dried over magnesium sulphate and evaporated. The residual yellow oil is purified by flash chromatography on silica eluting with initially with dichloro-methane then with a mixture of dichloromethane and ethyl acetate (9:1 v/v). Fractions homogeneous in the required products are evaporated to give methyl (E)-2-benzoylamino-3-(2,4-dibenzyloxyphenyl)acrylate (1 g) as a yellow foam, and methyl (Z)-2-benzoylamino-3-(2,4-dibenzyloxyphenyl)-acrylate (1.6 g) as a yellow oil.

후처리

  1. additionis added dropwise
  2. customevaporated
  3. customthe residue partitioned between ethyl acetate (100 mL) and water (75 mL)
  4. washThe organic phase is washed with brine (50 mL)
  5. dry with materialdried over magnesium sulphate
  6. customevaporated
  7. customThe residual yellow oil is purified by flash chromatography on silica eluting with initially with dichloro-methane
  8. additionwith a mixture of dichloromethane and ethyl acetate (9:1 v/v)
  9. customFractions homogeneous in the required products are evaporated

출처 및 근거

ORD 기록
ord-da2bc403b35c40529730b4aeab800d13
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06211234B1

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