Diisopropylamine → 3-Phenyl-2-t-butylcarboxymethylpropionic acid, ethyl ester

HRID 2259221노트

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HRID 2259221 반응식
C(N[CH:5]([CH3:7])[CH3:6])(C)C.[CH2:8]([Li])CCC.[C:13]([O:23][CH2:24][CH3:25])(=[O:22])[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Br[CH2:27][C:28]([O:30]C(C)(C)C)=[O:29]>O1CCCC1.CCCCCC>[C:16]1([CH2:15][C:14]([CH2:27][C:28]([OH:30])=[O:29])([C:5]([CH3:6])([CH3:7])[CH3:8])[C:13]([O:23][CH2:24][CH3:25])=[O:22])[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

참가 물질

7

반응물 4

HCID 7912DiisopropylamineHCID 16237Ethyl 3-phenylpropionateHCID 79177tert-Butyl bromoacetateHCID 178418339Butyllithium

생성물 1

HCID 867490123-Phenyl-2-t-butylcarboxymethylpropionic acid, ethyl ester수율 46%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

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온도
-78 °C

실험 절차

[4S-[4α, 7α(R*), 12bβ]]-7-[(1-Oxo-2-carboxymethyl-3-phenylpropyl)amino]-1,2,3,4,6,7,8,12b-octahydro-6-oxopyrido[2,1-a][2]benzazepine-4-carboxylic acid Dissolve diisopropylamine (3.5 mL, 25 mmol) in tetrahydrofuran (30 mL). Add n-butyllithium (14 mL of a 1.6M solution in hexane, 22.4 mmol). Stir for 15 minutes and cool to -78° C. Add, by dropwise addition, ethyl dihydrocinnamate (3.5 mL, 20 mmol) and stir for 30 minutes. Add t-butyl bromoacetate (4.0 mL, 25 mmol) and gradually warm to room temperature overnight. Quench the solution with ammonium chloride solution (10 mL) and partition between water (25 mL) and ethyl ether (50 mL). Separate the organic phase, dry (MgSO4) and evaporate the solvent in vacuo. Purify by silica gel chromatography (5% ethyl acetate/hexane) to give 3-phenyl-2-t-butylcarboxymethylpropionic acid, ethyl ester as a pale yellow oil (2.68 g, 46%).

후처리

  1. stirringstir for 30 minutes
  2. customQuench the solution with ammonium chloride solution (10 mL)
  3. custompartition between water (25 mL) and ethyl ether (50 mL)
  4. customSeparate the organic phase
  5. dry with materialdry (MgSO4)
  6. customevaporate the solvent in vacuo
  7. customPurify by silica gel chromatography (5% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-132e8f4e019f4f6890598c480a3829fe
출처 데이터셋
uspto-grants-1995_12
특허 번호
US05472959

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