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Lithium Hydroxide → (2S)-3-[4-(3-{4-[(tert-Butoxycarbonyl)amino]phenyl}propoxy)phenyl]-2-ethoxypropanoic acid

HRID 1375722
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HRID 1375722 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([CH2:25][C@H:26]([O:32][CH2:33][CH3:34])[C:27]([O:29]CC)=[O:28])=[CH:21][CH:20]=2)=[CH:11][CH:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH2:16][CH2:17][O:18][C:19]2[CH:20]=[CH:21][C:22]([CH2:25][C@H:26]([O:32][CH2:33][CH3:34])[C:27]([OH:29])=[O:28])=[CH:23][CH:24]=2)=[CH:13][CH:14]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 3939Lithium Hydroxide2회HCID 86613339Ethyl (2S)-3-[4-(3-{4-[(tert-butoxycarbonyl)amino]phenyl}propoxy)phenyl]-2-ethoxypropanoate

생성물 1

HCID 69424279(2S)-3-[4-(3-{4-[(tert-Butoxycarbonyl)amino]phenyl}propoxy)phenyl]-2-ethoxypropanoic acid수율 96%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran
용매

실험 절차

Ethyl (2S)-3-[4-(3-{4-[(tert-butoxycarbonyl)amino]phenyl}propoxy)phenyl]-2-ethoxypropanoate (350 mg, 0.742 mmol) was dissolved in THF (10 ml). Under stirring, lithium hydroxide in water (5 ml) was added. The mixture was stirred at room temperature and followed by HPLC. After 4 hours, the reaction was stopped. More lithium hydroxide (9 mg) was added. The mixture was stirred overnight. It was then evaporated in vacuum to remove THF. The residue was extracted with diethyl ether and then acidified with 10% hydrochloric acid, pH˜3, and extracted with ethyl acetate (×2). The organic phases were combined and washed with brine and dried with magnesium sulfate. The solvent was evaporated and white solid product (315 mg) was left, yield 96%.

후처리

  1. stirringThe mixture was stirred at room temperature
  2. stirringThe mixture was stirred overnight
  3. customIt was then evaporated in vacuum
  4. customto remove THF
  5. extractionThe residue was extracted with diethyl ether
  6. extractionextracted with ethyl acetate (×2)
  7. washwashed with brine
  8. dry with materialdried with magnesium sulfate
  9. customThe solvent was evaporated
  10. waitwhite solid product (315 mg) was left

출처 및 근거

ORD 기록
ord-8d393408841d4045afec8df5c8ded59f
출처 데이터셋
uspto-grants-2007_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07169810B2

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