Lithium Hydroxide → (+/-)-3-Phenyl-4-[4-[[[3-(pyridin-2-yl)amino-1-propyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoic acid

HRID 989903노트

반응식

HRID 989903 반응식
[C:1]1([CH:7]([CH2:14][C:15]2[O:16][CH:17]=[C:18]([C:20]([NH:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[O:21])[N:19]=2)[CH2:8][C:9]([O:11]CC)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[OH-]>C1COCC1.O>[C:1]1([CH:7]([CH2:14][C:15]2[O:16][CH:17]=[C:18]([C:20]([NH:22][CH2:23][CH2:24][CH2:25][NH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[O:21])[N:19]=2)[CH2:8][C:9]([OH:11])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 11189784Ethyl (+/-)-3-phenyl-4-[4-[[[3-(pyridin-2-yl)amino-1-propyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoate

생성물 1

HCID 9822714(+/-)-3-Phenyl-4-[4-[[[3-(pyridin-2-yl)amino-1-propyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoic acid수율 51.4%

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

실험 절차

To a solution of ethyl (±)-3-phenyl-4-[4-[[[3-(pyridin-2-yl)amino-1-propyl]amino]carbonyl]-1,3-oxazol-2-yl]butanoate (131 mg, 0.30 mmole) in 1:1 THF/H2O (10 mL) was added 1N LiOH (0.36 mL, 0.36 mmole). After 18 hr, the mixture was concentrated under reduced pressure. The residue was dissolved in 20 mL H2O then acidified to pH 6 using 10% HCl. The resulting cloudy solution was extracted with CH2Cl2 (3×75 mL). The organic extracts were dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was triturated with Et2O to give the title compound as a white solid (63 mg, 51%) which was collected by filtration. MS (ES) m/e 409 (M+H)+. Anal. Calcd for C22H24N4O4.0.75 H2O, 1.5 HCl: C, 55.44; H, 5.71; N, 11.75. Found: C, 55.49; H, 5.54; N, 11.63.

후처리

  1. concentrationthe mixture was concentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 20 mL H2O
  3. extractionThe resulting cloudy solution was extracted with CH2Cl2 (3×75 mL)
  4. dry with materialThe organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with Et2O

출처 및 근거

ORD 기록
ord-ca24fea2bb4e4459ae00c78152da7b25
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06458814B1

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