Hydrazine hydrate (1:1) → tert-butyl N-[1-amino-3-(methylsulfanyl)propan-2-yl]carbamate

HRID 1504834노트

반응식

HRID 1504834 반응식
O=C1C2C(=CC=CC=2)C(=O)[N:3]1[CH2:12][CH:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:14][S:15][CH3:16].O.NN>C(O)C>[NH2:3][CH2:12][CH:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:14][S:15][CH3:16]

참가 물질

4

반응물 2

HCID 24654Hydrazine hydrate (1:1)HCID 24720892tert-Butyl [2-phthalimido-1-(methylsulfanylmethyl)ethyl]carbamate

생성물 1

HCID 72455593tert-butyl N-[1-amino-3-(methylsulfanyl)propan-2-yl]carbamate

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of tert-butyl [1-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-(methylsulfanyl)propan-2-yl]carbamate (from Step 3 of PrepEx 4.11) (10.0 g, 28.6 mmol) in ethanol (150 mL) was added dropwise hydrazine hydrate (15.7 g, 286 mmol) at 0° C. and then the reaction mixture was allowed to warm to ambient temperature. After 30 minutes, the reaction mixture was heated to reflux. After two hours, the reaction mixture was cooled, filtered, and concentrated under reduced pressure. The residue was purified by chromatography on silica gel to give tert-butyl [1-amino-3-(methylsulfanyl)propan-2-yl]carbamate. MS ESI calc'd. for C9H21N2O2S [M+H]+ 221. found 221. 1H NMR (400 MHz, CD3OD) δ 3.66-3.63 (m, 1H), 2.83-2.79 (m, 1H), 2.64-2.50 (m, 3H), 2.12 (s, 3H), 1.45 (s, 9H).

후처리

  1. temperaturethe reaction mixture was heated to reflux
  2. waitAfter two hours
  3. temperaturethe reaction mixture was cooled
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-b40620f37a934282a7b5552bd37843b5
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216173B2

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