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Lithium Hydroxide → 4-[(4E)-3-(4-Carboxybenzyl)-5-{2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}pent-4-en-1-yl]-benzoic acid

HRID 1512223
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HRID 1512223 반응식
[OH-].[Li+].C[O:4][C:5]([C:7]1[CH:44]=[CH:43][C:10]([CH2:11][CH:12](/[CH:25]=[CH:26]/[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH2:34][CH2:35][CH2:36][N:37]2[CH2:41][CH2:40][CH2:39][C:38]2=[O:42])[CH2:13][CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21]C)=[O:20])=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)=[O:6]>C1COCC1.O>[C:5]([C:7]1[CH:8]=[CH:9][C:10]([CH2:11][CH:12](/[CH:25]=[CH:26]/[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH2:34][CH2:35][CH2:36][N:37]2[CH2:41][CH2:40][CH2:39][C:38]2=[O:42])[CH2:13][CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([OH:21])=[O:20])=[CH:17][CH:16]=2)=[CH:43][CH:44]=1)([OH:6])=[O:4]
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참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 59437424Methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-{2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}pent-4-en-1-yl]benzoate

생성물 1

HCID 249703434-[(4E)-3-(4-Carboxybenzyl)-5-{2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}pent-4-en-1-yl]-benzoic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran
용매

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온도
50 °C

실험 절차

492 mg (20.5 mmol) of lithium hydroxide are added to a solution of 3.90 g (6.8 mmol) of methyl 4-[(4E)-3-[4-(methoxycarbonyl)benzyl]-5-{2-[3-(2-oxopyrrolidin-1-yl)propoxy]phenyl}pent-4-en-1-yl]benzoate (Example 21A) in 20 ml of THF and 20 ml of water, and the mixture is stirred at 50° C. for 12 h. The mixture is then cooled and extracted three times with ethyl acetate. The aqueous phase is then adjusted to pH 2 using 1 M hydrochloric acid and extracted three times with ethyl acetate. The latter organic phases are combined, washed with water and saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is removed to dryness. This gives 2.75 g (content 98%, 4.98 mmol, 73% of theory) of the title compound as a colorless solid.

후처리

  1. temperatureThe mixture is then cooled
  2. extractionextracted three times with ethyl acetate
  3. extractionextracted three times with ethyl acetate
  4. washwashed with water and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. filtrationAfter filtration
  7. customthe solvent is removed to dryness

출처 및 근거

ORD 기록
ord-8372900194774e2d850ef0f169cca451
출처 데이터셋
uspto-grants-2012_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08217063B2

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