Water → HCID 86711485, 화합물

HRID 517545노트

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HRID 517545 반응식
[NH2:1][CH:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([Br:13])[CH:8]=1)[C:3]([OH:5])=[O:4].C([O-])(O)=O.[Na+].O.Cl[C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>C1COCC1>[Br:13][C:9]1[CH:8]=[C:7]([CH2:6][CH:2]([NH:1][C:21](=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:3]([OH:5])=[O:4])[CH:12]=[CH:11][CH:10]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 20884Ethoxalyl chlorideHCID 516892Sodium BicarbonateHCID 5540782-amino-3-(3-bromophenyl)propanoic acid

생성물 1

HCID 86711485HCID 86711485, 화합물수율 33.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a suspension of 2-amino-3-(3-bromophenyl)propanoic acid (11.0 g, 45.5 mmol) and NaHCO3 (11.5 g, 136.5 mmol) in THF (100 mL)/H2O (100 mL), ethyl 2-chloro-2-oxoacetate (18.4 g, 135.2 mmol) was added dropwise at 0° C. The mixture was stirred at RT overnight, acidified with aqueous critic acid (10%), and then extracted with EtOAc (3×100 mL). The combined organic layers were washed with H2O (100 mL) and brine (50 mL), dried over Na2SO4, filtered, and concentrated to afford the crude product, which was purified by Combiflash reverse phase chromatography (50%˜60% MeCN/H2O containing 0.01% TFA) to afford 3-(3-bromophenyl)-2-(2-ethoxy-2-oxoacetamido)propanoic acid as a colorless oil (5.2 g, 33%). MS (ES+) C13H14BrNO5 requires: 343, 345 found: 344 [M+H]+, 346 [M+2+H]+(1:1).

후처리

  1. additionwas added dropwise at 0° C
  2. extractionextracted with EtOAc (3×100 mL)
  3. washThe combined organic layers were washed with H2O (100 mL) and brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto afford the crude product, which
  8. customwas purified by Combiflash reverse phase chromatography (50%˜60% MeCN/H2O containing 0.01% TFA)

출처 및 근거

ORD 기록
ord-a64ee4ff200d4fa7995d28e8de8b6879
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09115120B2

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