Phenethylamine → Benzyl isovalerate

HRID 343970

반응식

HRID 343970 반응식
C(N(CC)CC)C.[CH2:8](CN)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)[C:28]2C=CC=[CH:32][C:27]=2N=N1.[C:44]([O:47]CC)(=[O:46])[CH3:45]>C(Cl)Cl>[CH2:8]([O:47][C:44](=[O:46])[CH2:45][CH:27]([CH3:32])[CH3:28])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

참가 물질

6

반응물 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

생성물 1

HCID 7651Benzyl isovalerate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-(R)-2-[carboxymethyl(4-methoxybenzenesulfonyl)amino]-3-methylbutyric acid benzyl ester (Example 1) (1.05 grams, 2.41 mmol) in methylene chloride (20 mL) were added sequentially triethylamine (0.84 mL, 6.0 mmol),N-benzylmethylamine (0.34 mL, 2.63 mmol) and (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (1.17 grams, 2.69 mmol). The mixture was stirred at room temperature overnight and then diluted with ethyl acetate. The solution was washed with 0.5N hydrochloric acid solution and brine, dried over magnesium sulfate and concentrated under vacuum. The residue was chromatographed on silica gel using 35% ethyl acetate in hexane (plus a small amount of methylene chloride to load the sample on the column) affording 2-(R)-2-[benzylmethylcarbamoylmethyl)(4-methoxybenzenesulfonyl)amino]-3-methylbutyric acid benzyl ester as a clear oil, 1.14 grams (88%).

후처리

  1. washThe solution was washed with 0.5N hydrochloric acid solution and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue was chromatographed on silica gel using 35% ethyl acetate in hexane (plus a small amount of methylene chloride

출처 및 근거

ORD 기록
ord-1c301499333d4c0b96ddb53ab9809753
출처 데이터셋
uspto-grants-1999_01
특허 번호
US05863949

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