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Water → 6-fluoro-5-[(S)-(pyrrolidin-3-ylsulfanyl)]-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one

HRID 1633800
ノート
印刷プレビュー

反応式

HRID 1633800 の反応式
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([S:13][C:14]2[CH:15]=[C:16]([C:28]3[NH:29][CH:30]=[CH:31][CH:32]=3)[C:17]3[C:18](=[O:27])[NH:19][C:20]4[C:25]=3[C:24]=2[C:23]([F:26])=[CH:22][CH:21]=4)[CH2:9]1)=O)(C)(C)C.O>C(O)(C(F)(F)F)=O.C(Cl)Cl>[F:26][C:23]1[C:24]2[C:25]3[C:20](=[CH:21][CH:22]=1)[NH:19][C:18](=[O:27])[C:17]=3[C:16]([C:28]1[NH:29][CH:30]=[CH:31][CH:32]=1)=[CH:15][C:14]=2[S:13][C@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 962WaterHCID 12042976(S)-3-[6-fluoro-2-oxo-3-(1H-pyrrol-2-yl)-1,2-dihydro-benzo[cd]indol-5-ylsulfanyl]-pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 100666566-fluoro-5-[(S)-(pyrrolidin-3-ylsulfanyl)]-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 6422Trifluoroacetic acid
溶媒

実験手順

(S)-3-[6-Fluoro-2-oxo-3-(1H-pyrrol-2-yl)-1,2-dihydro-benzo[cd]indol-5-ylsulfanyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (from Example 56 above) (54 mg, 0.12 mmol) was dissolved at 0° C. in a 50% TFA in CH2Cl2 solution (6 mL) that contained H2O (0.3 mL). After 2 hours the reaction mixture was partitioned between ethyl acetate and aqueous 1N NaOH. The pH of the aqueous layer was adjusted to 14. The aqueous layer was extracted twice with ethyl acetate and the combined organic layer was washed with H2O, dried over Na2SO4, filtered, and concentrated to dryness. The residue was purified by a precipitation out of THF with excess of pentane to give 6-fluoro-5-[(S)-(pyrrolidin-3-ylsulfanyl)]-3-(1H-pyrrol-2-yl)-1H-benzo[cd]indol-2-one as a yellow solid. (Yield 41 mg; 97%).

後処理

  1. customAfter 2 hours the reaction mixture was partitioned between ethyl acetate and aqueous 1N NaOH
  2. extractionThe aqueous layer was extracted twice with ethyl acetate
  3. washthe combined organic layer was washed with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe residue was purified by a precipitation out of THF with excess of pentane

出典と根拠

ORDレコード
ord-11309eff12434505a39e25f8c60b1297
出典データセット
uspto-grants-2003_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06504034B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート