Triethylamine → (S)-3-((tert-Butoxycarbonyl)amino)-5-fluoro-4-oxopentanoic acid

HRID 368931

반응식

HRID 368931 반응식
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[CH2:3][C:4](=[O:6])[OH:5].[F:17][CH2:18]C(OC(=O)CF)=O.C(N(CC)CC)C>C1C=CC=CC=1.CN(C)C1C=CN=CC=1>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([CH2:18][F:17])=[O:9])[CH2:3][C:4](=[O:6])[OH:5]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 67886Acetic acid, 2-fluoro-, 1,1'-anhydrideHCID 99718N-(tert-butoxycarbonyl)-L-aspartic acid

생성물 1

HCID 10131156(S)-3-((tert-Butoxycarbonyl)amino)-5-fluoro-4-oxopentanoic acid

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 241Benzene용매2회

실험 절차

A suspension of Boc-Asp-OH (8.11 mmol) and fluoroacetic anhydride (16.2 mmol) in benzene (30 ml) was treated with triethylamine (16.2 mmol) at room temperature. The catalyst 4-dimethylaminopyridine (0.41 mmol) was added to the solution and the reaction stirred for about 2 h at room temperature. About 100 ml benzene was added to the reaction mixture. The organic solution was washed with 1N HCl (2×50 ml), saturated NaHCO3 (2×50 ml), and saturated NaCl (2×50 ml), followed by drying over anhydrous MgSO4. The solvent was then removed by evaporation under reduced pressure. The resulting oil was applied to a 2.5×80 cm column of silica gel (60-200 mesh). The title compound was eluded with 2% methanol in chloroform.

후처리

  1. washThe organic solution was washed with 1N HCl (2×50 ml), saturated NaHCO3 (2×50 ml), and saturated NaCl (2×50 ml)
  2. dry with materialby drying over anhydrous MgSO4
  3. customThe solvent was then removed by evaporation under reduced pressure

출처 및 근거

ORD 기록
ord-d404ed8a393943249af15d1d9d99dbdc
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06136787

연결된 노트

불러오는 중…