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Lithium Hydroxide → Trans-2-carboxy-5,7-dichloro-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline

HRID 484436
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HRID 484436 반응식
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C@@H:4]([NH:17][C:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[C:5](=C=O)[C@H:6](OC)[NH:7]2.[OH-:27].[Li+].[O:29]1[CH2:33]CCC1>O>[C:33]([C@H:6]1[CH2:5][C@H:4]([NH:17][C:18]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:19])[C:3]2[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[NH:7]1)([OH:29])=[O:27]
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참가 물질

5

반응물 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86747046trans-5,7-Dichloro-2-methoxy-carbonyl-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline

생성물 1

HCID 15168526Trans-2-carboxy-5,7-dichloro-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a suspension of trans-5,7-dichloro-2-methoxy-carbonyl-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline (3.11 g, 7.89 mmol) in a mixture of tetrahydrofuran (100 ml) and water (50 ml) was added aqueous lithium hydroxide (17.4 ml of a 0.5M solution, 8.70 mmol) and the resulting mixture was stirred at room temperture for 3 h. The organic solvent was removed in vacuo and the aqueous residue was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (2×100 ml). The combined extracts were washed with saturated brine (1×100 ml), dried (MgSO4) and evaporated to give the crude product which was recrystallised from ethyl acetate/petroleum ether 60-80 to give the title compound as colourless crystals (2 crops, 2.65 g) identical in physical properties to example 34 step b.

후처리

  1. customThe organic solvent was removed in vacuo
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. washThe combined extracts were washed with saturated brine (1×100 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give the crude product which
  7. customwas recrystallised from ethyl acetate/petroleum ether 60-80

출처 및 근거

ORD 기록
ord-e988fd1a59784dc194f8c048ca209ffd
출처 데이터셋
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05231102

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