Lithium Hydroxide → (2S)-3-Methyl-2-({[methyl(pent-4-en-1-yl)amino]carbonyl}amino)butanoic acid

HRID 1360107노트

반응식

HRID 1360107 반응식
[CH3:1][CH:2]([CH3:18])[C@H:3]([NH:8][C:9]([N:11]([CH3:17])[CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16])=[O:10])[C:4]([O:6]C)=[O:5].[Li+].[OH-]>C1COCC1>[CH3:1][CH:2]([CH3:18])[C@H:3]([NH:8][C:9]([N:11]([CH3:17])[CH2:12][CH2:13][CH2:14][CH:15]=[CH2:16])=[O:10])[C:4]([OH:6])=[O:5]

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 57617072Methyl (2S)-3-methyl-2-({[methyl(pent-4-en-1-yl)amino]carbonyl}amino)butanoate

생성물 1

HCID 57617111(2S)-3-Methyl-2-({[methyl(pent-4-en-1-yl)amino]carbonyl}amino)butanoic acid수율 95%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A 250 mL round bottom flask under nitrogen was charged with methyl (2S)-3-methyl-2-({[methyl(pent-4-en-1-yl)amino]carbonyl}amino)butanoate from the previous step, THF (40 mL), and aqueous LiOH (1 M, 60 mmol, 60 mL). The reaction mixture was stirred 18 hours. THF was removed by evaporation. The remaining aqueous mixture was poured into water and washed once with EtOAc. The aqueous layer was acidified with 1 M hydrochloric acid and extracted with EtOAc (3×). Combined organic extracts were dried with anhydrous NaSO4, filtered and evaporated to give the title compound as a pale oil (2.34 g, 9.66 mmol, 95%). LRMS m/e [M+H]+ 243.

후처리

  1. customTHF was removed by evaporation
  2. additionThe remaining aqueous mixture was poured into water
  3. washwashed once with EtOAc
  4. extractionextracted with EtOAc (3×)
  5. dry with materialCombined organic extracts were dried with anhydrous NaSO4
  6. filtrationfiltered
  7. customevaporated

출처 및 근거

ORD 기록
ord-6f875324f5ce4552b958e58cd1965207
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879797B2

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