Hydrazine → tert-butyl N-(2-aminoethyl)-3-methyl-L-valinate

HRID 1174297노트

반응식

HRID 1174297 반응식
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH2:13][NH:14][C@H:15]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:16]([CH3:19])([CH3:18])[CH3:17].NN>C(O)C>[NH2:3][CH2:12][CH2:13][NH:14][C@H:15]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:16]([CH3:18])([CH3:19])[CH3:17]

참가 물질

4

반응물 2

HCID 9321HydrazineHCID 67407870tert-butyl(2S)-2-{[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]amino}-3,3-dimethylbutanoate

생성물 1

HCID 86599577tert-butyl N-(2-aminoethyl)-3-methyl-L-valinate수율 93.2%

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
75 °C

실험 절차

The product of Example 111-2 (87 g, 241.6 mmol) was taken up in ethanol (2 L) in a 3-necked, 3L round bottom flask equipped with mechanical stirring under N2. Hydrazine (anhydrous, 68.3 mL, 2.17 mol, 9 equivalents) was added. The reaction mixture was heated to 75° C., which resulted in the formation of a very thick suspension. The addition of more ethanol was necessary in order to continue effective stirring. The reaction was stirred for 1 hour at 75° C. until consumption of starting material was complete as determined by HPLC. The thick suspension was cooled to ambient temperature and quenched with 1 L of 0.5N NaOH solution. The mixture was diluted with 0.5N NaOH (2 L) and extracted with dichloromethane (2×2 L). The combined organic layer was washed with brine (1 L), dried over MgSO4, filtered and concentrated to oil. The oil was chased with heptanes to remove ethanol and pump dried to afford light yellow oil (50.2 g, 93.2% yield). 1H NMR (CDCl3): δ 2.73(m, 4H), 2.45(m, 1H), 1.64(s, 9H), 0.96(s, 9H).

후처리

  1. customequipped
  2. customwhich resulted in the formation of a very thick suspension
  3. stirringThe reaction was stirred for 1 hour at 75° C. until consumption of starting material
  4. temperatureThe thick suspension was cooled to ambient temperature
  5. customquenched with 1 L of 0.5N NaOH solution
  6. additionThe mixture was diluted with 0.5N NaOH (2 L)
  7. extractionextracted with dichloromethane (2×2 L)
  8. washThe combined organic layer was washed with brine (1 L)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated to oil
  12. customto remove ethanol and pump
  13. customdried

출처 및 근거

ORD 기록
ord-f6fbb4d3ee6148068649d2b86f1a743b
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07834043B2

반응 노트

불러오는 중…