Water → HCID 86711485、化合物

HRID 517545ノート

反応式

HRID 517545 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 86711485HCID 86711485、化合物収率 33.2%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a64ee4ff200d4fa7995d28e8de8b6879
出典データセット
uspto-grants-2015_08
特許番号
US09115120B2

反応ノート

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