Sodium Hydroxide → N-[(4-chloro-3-ethylphenyl)methyl]5-hydroxyindole-2-carboxylic Acid

HRID 1610925노트

반응식

HRID 1610925 반응식
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([O:20]C(=O)C)=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:24]([O:26]CC)=[O:25])=[CH:6][C:5]=1[C:29]#[C:30][Si](C)(C)C>CO.O.C(OCC)(=O)C.CCCC(C)C>[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([OH:20])=[CH:17][CH:18]=3)[CH:13]=[C:12]2[C:24]([OH:26])=[O:25])=[CH:6][C:5]=1[CH2:29][CH3:30]

참가 물질

7

반응물 2

HCID 14798Sodium HydroxideHCID 22259369ethyl N-[(4-chloro-3-trimethylsilylethynylphenyl)methyl]-5-acetoxyindole-2-carboxylate

생성물 1

HCID 22259372N-[(4-chloro-3-ethylphenyl)methyl]5-hydroxyindole-2-carboxylic Acid수율 65.9%

시약·촉매·용매 4

HCID 887Methanol용매HCID 962Water용매HCID 78922-Methylpentane용매HCID 8857Ethyl Acetate용매

실험 절차

Sodium hydroxide (2M, 1.8 ml) was added to a solution of ethyl N-[(4-chloro-3-trimethylsilylethynylphenyl)methyl]-5-acetoxyindole-2-carboxylate (0.14 g) in methanol (5 ml) and the mixture was stirred for 3 hours. The methanol was removed and the residue obtained was diluted with water (20 ml) and extracted twice with ethyl acetate (20 ml each time). The aqueous layer was acidified with aqueous hydrochloric acid (2M) and extracted with ethyl acetate (3×25 ml). The combined ethyl acetate extracts were washed with water (30 ml) and brine (30 ml) and dried (MgSO4). The residue obtained on removal of the solvent was dissolved in a mixture of ethyl acetate and iso-hexane (1:1) and passed down a 5 g silica Isolute column eluting with an ethyl acetate iso-hexane mixture (1:1) to give the title compound (65 mg). NMR (CD3SOCD3): d 4.5 (s, 1H), 5.7 (s, 2H), 6.8 (m, 1H), 6.9 (m, 2H), 7.1 (m, 1H), 7.2 (s, 1H), 7.35 (m, 1H), 7.4 (m, 2H), 9.0 (s, 1H); m/z 324.4 (M−H).

후처리

  1. customThe methanol was removed
  2. customthe residue obtained
  3. extractionextracted twice with ethyl acetate (20 ml each time)
  4. extractionextracted with ethyl acetate (3×25 ml)
  5. washThe combined ethyl acetate extracts were washed with water (30 ml) and brine (30 ml)
  6. dry with materialdried (MgSO4)
  7. customThe residue obtained on removal of the solvent
  8. washeluting with an ethyl acetate iso-hexane mixture (1:1)

출처 및 근거

ORD 기록
ord-51ca09b46412458fae7bb2a7028d19d0
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06984657B1

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