Ninhydrin → Methyl (R)-2-Amino-3-(trimethylsilyl)propanoate

HRID 719110

반응식

HRID 719110 반응식
[CH3:1][Si:2]([CH3:10])([CH3:9])[CH2:3][C@@H:4]([C:6]([OH:8])=[O:7])[NH2:5].B(F)(F)F.CO.[CH:17]1C=C2C(C(O)(O)C(=O)C2=CC=1)=O.C([O-])([O-])=O.[Na+].[Na+]>C(O)C.O.CCOC(C)=O.CO.C(Cl)Cl>[CH3:1][Si:2]([CH3:10])([CH3:9])[CH2:3][C@@H:4]([C:6]([O:8][CH3:17])=[O:7])[NH2:5]

참가 물질

9

반응물 4

HCID 10236NinhydrinHCID 10340Sodium Carbonate2회HCID 11008231(2R)-2-amino-3-(trimethylsilyl)propanoic acidHCID 11062313Boron, trifluoro(methanol)-, (T-4)-

생성물 1

HCID 59302397Methyl (R)-2-Amino-3-(trimethylsilyl)propanoate수율 92%

시약·촉매·용매 4

HCID 702Ethanol용매HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 21226129Dichloromethane methanol용매

반응 조건

온도
70 °C

실험 절차

3-Trimethylsilyl alanine (J. Organomet. Chem., 628, (2001), 183–194; 19 mg, 0.118 mmol) was mixed with 3 ml BF3-MeOH (14%, 3.7 mmol) in a sealed tube and heated to 70° C. Analysis was performed using TLC (MeOH:DCM 1:9, stained w. ninhydrine in ethanol). The mixture was heated for 3 h and was then cooled to ambient temperature. The mixture was poured into a mixture of 3 ml EtOAc and 2 ml water containing Na2CO3. More Na2CO3 (5%-aq) was added until pH ca 7. The aqueous phase was washed with EtOAc (2×3 ml). The combined organic layers were washed with brine (1 ml), dried with Na2SO4 and evaporated. The product was obtained as a white film. Mass: 19 mg (92% yield). NMR (CDCl3): 0.1 (s, 9H), 1.2–1.4 (m, 2H), 3.8 (s, 3H), 4.2 (brs, 1H).

후처리

  1. temperatureThe mixture was heated for 3 h
  2. temperaturewas then cooled to ambient temperature
  3. washThe aqueous phase was washed with EtOAc (2×3 ml)
  4. washThe combined organic layers were washed with brine (1 ml)
  5. dry with materialdried with Na2SO4
  6. customevaporated
  7. customThe product was obtained as a white film

출처 및 근거

ORD 기록
ord-5929ac61b44f44a68d65dad6554dcc85
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132416B2

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