Ethanol → 1,1-dimethylethyl (3S)-3-(2-hydrazino-2-oxoethyl)-1-pyrrolidinecarboxylate

HRID 525154노트

반응식

HRID 525154 반응식
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([CH2:13][C:14]([OH:16])=O)[CH2:9]1)=[O:7])([CH3:4])[CH3:3].C(O)C.O.[NH2:21][NH2:22]>C(OCC)C.CN(C)C1C=CN=CC=1>[NH:21]([C:14](=[O:16])[CH2:13][C@@H:10]1[CH2:11][CH2:12][N:8]([C:6]([O:5][C:2]([CH3:4])([CH3:3])[CH3:1])=[O:7])[CH2:9]1)[NH2:22]

참가 물질

6

반응물 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 1502098(S)-2-(1-(tert-butoxycarbonyl)pyrrolidin-3-yl)acetic acid

생성물 1

HCID 866748261,1-dimethylethyl (3S)-3-(2-hydrazino-2-oxoethyl)-1-pyrrolidinecarboxylate수율 88%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 3283Diethyl Ether용매2회

실험 절차

A solution of ((3S)-1-{[(1,1-dimethylethyl)oxy]carbonyl}-3-pyrrolidinyl)acetic acid (5 g, 21.81 mmol) in diethyl ether (50 mL) was treated with N,N-dimethyl-4-pyridinamine (2.181 mmol), N-[3-(dimethylamino)propyl]-N-ethylcarbodiimide(HCl) (23.99 mmol), and ethanol (48.0 mmol) and was stirred at room temperature overnight. Analysis by LCMS indicated that all starting material had converted to the desired methyl ester. The reaction contents were diluted with ether (100 mL) and washed with saturated aq NaHSO4 solution, water, and brine. The organic phase was dried over magnesium sulfate, filtered and concentrated to dryness in vacuo. The resulting clear oil was dissolved in ethanol (25 mL), treated with hydrazine monohydrate (436 mmol), and was stirred overnight at 80° C. LCMS analysis indicated complete conversion of the intermediate. The reaction solution was concentrated to dryness in vacuo to afford the title compound as a clear oil (4.65 grams, 88% yield). No further purification was utilized. MS(ES)+ m/e 244.2 [M+H]+.

후처리

  1. customThe reaction contents
  2. washwashed with saturated aq NaHSO4 solution, water, and brine
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness in vacuo
  6. dissolutionThe resulting clear oil was dissolved in ethanol (25 mL)
  7. stirringwas stirred overnight at 80° C
  8. concentrationThe reaction solution was concentrated to dryness in vacuo

출처 및 근거

ORD 기록
ord-5d91d577350244f58aa16de36dfcd507
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340529B2

반응 노트

불러오는 중…