Ammonium Chloride → HCID 59497521, 화합물

HRID 388488

반응식

HRID 388488 반응식
[CH2:1]([NH:8][C@@H:9]([CH3:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[C:22]([O:29][CH2:30][CH3:31])(=[O:28])/[CH:23]=[CH:24]/[CH2:25][CH2:26][CH3:27].[NH4+].[Cl-]>C1COCC1>[CH2:30]([O:29][C:22](=[O:28])[CH2:23][C@@H:24]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C@H:9]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH3:16])[CH2:25][CH2:26][CH3:27])[CH3:31]

참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 1268085(S)-(-)-N-Benzyl-1-phenylethylamineHCID 5364778Ethyl trans-2-hexenoateHCID 178418339Butyllithium

생성물 1

HCID 59497521HCID 59497521, 화합물수율 50.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

To a solution of (S)-(−)-N-benzyl-alpha-methyl-benzylamine (50 mL, 239 mmol) in THF (150 mL) at 0° C. is added nBuLi (2.5 M in THF) (100 mL, 250 mmol) under nitrogen atmosphere. The solution is cooled to −78° C. and ethyl trans-2-hexenoate (16.6 g, 117 mmol) is added. The solution is stirred for 1 hour and saturated NH4Cl solution is added. The solution is warmed to room temperature and is extracted with EtOAc. The combined organic layer is dried with MgSO4 and is filtered. The filtrate is concentrated and the residue is purified by flash chromatography with 5% EtOAc in Hexane as the eluent to afford the (S)-3-[Benzyl-((S)-1-phenyl-ethyl)-amino]-hexanoic acid ethyl ester (20.8 g, 50%) as a colorless oil.

후처리

  1. temperatureThe solution is warmed to room temperature
  2. extractionis extracted with EtOAc
  3. dry with materialThe combined organic layer is dried with MgSO4
  4. filtrationis filtered
  5. concentrationThe filtrate is concentrated
  6. customthe residue is purified by flash chromatography with 5% EtOAc in Hexane as the eluent

출처 및 근거

ORD 기록
ord-46acb57131954e39b0b4a0339f750930
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08377949B2

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