Lithium hydroxide, monohydrate → [({5-[(1R)-1-(2-tert-butoxy-2-oxoethyl)-4-cyclohexylbutyl]-1,2,4-oxadiazol-3-yl}methyl)(methyl)amino]acetic acid

HRID 2084490노트

반응식

HRID 2084490 반응식
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([CH2:24][N:25]([CH2:27][C:28]([O:30]CC)=[O:29])[CH3:26])[N:20]=2)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[Li].O>O1CCOCC1.O>[C:15]([O:14][C:12](=[O:13])[CH2:11][C@H:10]([C:19]1[O:23][N:22]=[C:21]([CH2:24][N:25]([CH2:27][C:28]([OH:30])=[O:29])[CH3:26])[N:20]=1)[CH2:9][CH2:8][CH2:7][CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1)([CH3:18])([CH3:16])[CH3:17]

참가 물질

5

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 60077674tert-butyl(3R)-6-cyclohexyl-3-(3-{[(2-ethoxy-2-oxoethyl)(methyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate

생성물 1

HCID 60077601[({5-[(1R)-1-(2-tert-butoxy-2-oxoethyl)-4-cyclohexylbutyl]-1,2,4-oxadiazol-3-yl}methyl)(methyl)amino]acetic acid수율 120.7%

시약·촉매·용매 2

HCID 962Water용매HCID 312751,4-Dioxane용매

실험 절차

A solution of tert-butyl (3R)-6-cyclohexyl-3-(3-([(2-ethoxy-2-oxoethyl)(methyl)amino]methyl}-1,2,4-oxadiazol-5-yl)hexanoate (preparation 132) (1.00 g, 2.21 mmol) in dioxan (20 ml) and H2O (20 ml) was treated with LiOH.H2O (193 mg, 2.21 mmol) and the reaction mixture stirred at room temperature for 19 hours. The solvent was removed under reduced pressure. The residue was dissolved in EtOAc and washed with brine. The aqueous was extracted with EtOAc (×3). The combined organic extracts were dried over anhydrous Na2SO4 and filtered. The solvent was removed under reduced pressure to afford the title compound as a white foam (1.13 g).

후처리

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with brine
  4. extractionThe aqueous was extracted with EtOAc (×3)
  5. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  6. filtrationfiltered
  7. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-2a6f5e8d08774121b50c15877372524d
출처 데이터셋
uspto-grants-2004_04
특허 번호
US06716861B2

반응 노트

불러오는 중…