Acetic Acid → 2-tert-Butoxycarbonylamino-3-(4-fluoro-phenylamino)-2-methyl-propionic acid methyl ester

HRID 491761노트

반응식

HRID 491761 반응식
[CH3:1][O:2][C:3](=[O:16])[C:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:7])[CH:5]=O.[F:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH3:1][O:2][C:3](=[O:16])[C:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])([CH3:7])[CH2:5][NH:22][C:21]1[CH:23]=[CH:24][C:18]([F:17])=[CH:19][CH:20]=1

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 97314-FluoroanilineHCID 5003444Sodium cyanoborohydrideHCID 22630101Methyl 2-[(tert-butoxycarbonyl)amino]-2-methyl-3-oxopropanoate

생성물 1

HCID 576789232-tert-Butoxycarbonylamino-3-(4-fluoro-phenylamino)-2-methyl-propionic acid methyl ester수율 53.2%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

To a solution of 2-tert-butoxycarbonylamino-2-methyl-3-oxo-propionic acid methyl ester (2.35 g, 6.71 mmol) in methanol (25 mL) was added 4-fluoroaniline (0.53 mL, 5.59 mmol) and acetic acid (0.16 mL, 2.80 mmol). A solution of sodium cyanoborohydride (188 mg, 2.99 mmol) in methanol (25 mL) was added dropwise and the reaction mixture stirred for 3 hours at room temperature post addition. The solvent was removed in vacuo and the residue dissolved in DCM (50 mL). The organic solution was treated with aqueous sodium carbonate solution (20 mL, 1N), stirred for 20 min, and the aqueous layer removed. Concentration of the organic layer followed by purification of the residue using flash chromatography (SiO2, DCM) afforded the title compound as a yellow oil (970 mg, 53%).

후처리

  1. additionpost addition
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in DCM (50 mL)
  4. additionThe organic solution was treated with aqueous sodium carbonate solution (20 mL, 1N)
  5. stirringstirred for 20 min
  6. customthe aqueous layer removed
  7. customConcentration of the organic layer followed by purification of the residue

출처 및 근거

ORD 기록
ord-d3602da0734447b5b59800747451b449
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531565B2

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