Acetic Acid → 5-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-hydroxymethyl-2-oxo-2-phenylethyl)amide

HRID 751733노트

반응식

HRID 751733 반응식
[Si]([O:8][CH2:9][C@H:10]([NH:19][C:20]([C:22]1[NH:31][C:25]2=[CH:26][N:27]=[C:28]([Cl:30])[CH:29]=[C:24]2[CH:23]=1)=[O:21])[C:11](=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>C1COCC1.O>[OH:8][CH2:9][C@H:10]([NH:19][C:20]([C:22]1[NH:31][C:25]2=[CH:26][N:27]=[C:28]([Cl:30])[CH:29]=[C:24]2[CH:23]=1)=[O:21])[C:11](=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

참가 물질

7

반응물 4

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 597535505-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S)-(tert-butyldimethylsilanyloxymethyl)-2-oxo-2-phenylethyl]amide

생성물 1

HCID 597536965-Chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid (1-(S)-hydroxymethyl-2-oxo-2-phenylethyl)amide

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylic acid [1-(S) -(tert-butyldimethylsilanyloxymethyl)-2-oxo-2-phenylethyl]amide (Preparation 101, 220 mg, 0.48 mmol) in THF (10 mL) was added acetic acid (60 μL) and tetrabutylammonium fluoride solution (1 ml, 1M in THF) at rt. After stirring for 3 h the reaction mixture was distributed between ethyl acetate (100 mL) and water (30 mL). The organic layer was separated, then washed with brine (50 ml), dried (MgSO4) and concentrated to a solid residue. Recrystallisation from THF gave the title compound.

후처리

  1. customThe organic layer was separated
  2. washwashed with brine (50 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to a solid residue
  5. customRecrystallisation from THF

출처 및 근거

ORD 기록
ord-0eedd35946f049bc88156b8759a0742b
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405210B2

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