Ethyl oxoacetate → Ethyl 2-((4-chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl)amino)acetate

HRID 588871노트

반응식

HRID 588871 반응식
[Cl:1][C:2]1[C:8]([C:9]2([CH3:12])[CH2:11][CH2:10]2)=[CH:7][C:5]([NH2:6])=[C:4]([O:13][CH3:14])[CH:3]=1.[C:15]([O:19][CH2:20][CH3:21])(=[O:18])[CH:16]=O.C([BH3-])#N.[Na+]>CO.CC(O)=O>[Cl:1][C:2]1[C:8]([C:9]2([CH3:12])[CH2:10][CH2:11]2)=[CH:7][C:5]([NH:6][CH2:16][C:15]([O:19][CH2:20][CH3:21])=[O:18])=[C:4]([O:13][CH3:14])[CH:3]=1

참가 물질

6

반응물 3

HCID 70211Ethyl oxoacetateHCID 5003444Sodium cyanoborohydrideHCID 904558234-Chloro-2-methoxy-5-(1-methylcyclopropyl)aniline

생성물 1

HCID 90456166Ethyl 2-((4-chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl)amino)acetate수율 100.3%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 887Methanol용매

실험 절차

To a solution of 4-chloro-2-methoxy-5-(1-methylcyclopropyl)aniline (450 mg, 2.13 mmol) in MeOH (20 mL) at RT, AcOH (3 drops) and ethyl glyoxalate (326 mg, 3.19 mmol, 50% in toluene) were added. The mixture was stirred at RT for 2 h and then sodium cyanoborohydride (403 mg, 6.39 mmol) was added to the mixture. The resulting mixture was stirred at 50° C. for 16 h. The mixture was allowed to cool to RT, and partitioned between ethyl acetate and water. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo to afford the crude product (636 mg). ESI-MS m/z: 298.2[M+H]+.

후처리

  1. stirringThe resulting mixture was stirred at 50° C. for 16 h
  2. temperatureto cool to RT
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f234432b94514c0daab7cd99b2ab5ce2
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227978B2

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