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Lithium Hydroxide → (2S,4R)-1-((2S,3S)-2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoyl)-4-hydroxypyrrolidine-2-carboxylic acid

HRID 523180
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HRID 523180 반응식
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:22]([O:25][C@@H:26]([CH2:28][CH2:29][CH:30]=[CH2:31])[CH3:27])[CH2:23][CH3:24])[C:10]([N:12]1[CH2:16][C@H:15]([OH:17])[CH2:14][C@H:13]1[C:18]([O:20]C)=[O:19])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.[OH-].[Li+]>CO>[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@@H:22]([O:25][C@@H:26]([CH2:28][CH2:29][CH:30]=[CH2:31])[CH3:27])[CH2:23][CH3:24])[C:10]([N:12]1[CH2:16][C@H:15]([OH:17])[CH2:14][C@H:13]1[C:18]([OH:20])=[O:19])=[O:11])=[O:7])([CH3:2])([CH3:4])[CH3:3]
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참가 물질

5

반응물 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 90117961(2S,4R)-methyl 1-((2S,3S)-2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoyl)-4-hydroxypyrrolidine-2-carboxylate2회

생성물 1

HCID 90118022(2S,4R)-1-((2S,3S)-2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoyl)-4-hydroxypyrrolidine-2-carboxylic acid수율 82.1%

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

To a round-bottom flask equipped with a stir bar was added (2S,4R)-methyl 1-((2S,3S)-2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoyl)-4-hydroxypyrrolidine-2-carboxylate (all material from step 2, 1.39 mmol), THF (5 mL) and MeOH (5 mL). To the solution was added aq. lithium hydroxide (2.0 M, 4.51 mmol). The mixture was stirred at room temperature for 16 h; then was concentrated to afford an aqueous solution. This solution was acidified and then transferred to a separatory funnel. The solution was twice extracted with EtOAc. The combined organics were washed with brine; dried over MgSO4; filtered; then concentrated in vacuo to afford (2S,4R)-1-((2S,3S)-2-((tert-butoxycarbonyl)amino)-3-((R)-hex-5-en-2-yloxy)pentanoyl)-4-hydroxypyrrolidine-2-carboxylic acid as a white solid (489 mg).

후처리

  1. customTo a round-bottom flask equipped with a stir bar
  2. concentrationthen was concentrated
  3. customto afford an aqueous solution
  4. customtransferred to a separatory funnel
  5. extractionThe solution was twice extracted with EtOAc
  6. washThe combined organics were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationthen concentrated in vacuo

출처 및 근거

ORD 기록
ord-b4109bbc7c144a34b6552217c8b6fa22
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09334279B2

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