N-(4-Methoxybenzylidene)glycine methyl ester → N-((4-Methoxyphenyl)methyl)glycine methyl ester

HRID 722447노트

반응식

HRID 722447 반응식
[CH3:1][O:2][C:3](=[O:15])[CH2:4][N:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1.[BH4-].[Na+]>C1COCC1.CO>[CH3:1][O:2][C:3](=[O:15])[CH2:4][NH:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=1

참가 물질

5

반응물 2

HCID 4193973N-(4-Methoxybenzylidene)glycine methyl esterHCID 4311764Sodium borohydride

생성물 1

HCID 10846084N-((4-Methoxyphenyl)methyl)glycine methyl ester

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-5 °C

실험 절차

To a solution of 91.3 g (0.441 mol) of [(4-methoxy-benzylidene)-amino]-acetic acid methyl ester in 500 ml of THF and 1000 ml of MeOH, 20 g (0.529 mol) of sodium borohydride is added portionwise at −10 to 0° C. The reaction mixture is stirred for 30 min. at −10 to 0° C. and quenched with sat. NH4Cl. After adding of ice-water, the mixture is concentrated to ¼ of whole volume and extracted with AcOEt. The combined extracts are washed with H2O and brine, dried over MgSO4 and concentrated under reduced pressure to give (4-methoxybenzylamino)-acetic acid methyl ester; NMR (CDCl3): 1.87 (br s, 1H), 3.41 (s, 2H), 3.73 (s, 3H), 3.74 (s, 2H), 3.8 (s, 3H), 6.86 (d, 2H, J=8.56 Hz), 7.24 (d, 2H, J=8.56 Hz).

후처리

  1. customquenched with sat. NH4Cl
  2. additionAfter adding of ice-water
  3. concentrationthe mixture is concentrated
  4. extractionextracted with AcOEt
  5. washThe combined extracts are washed with H2O and brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-a9b116057f5043d9acdbe7f7a69de1ee
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138432B1

반응 노트

불러오는 중…