Hydrochloric Acid → (s)-1-(2-Hydroxyethyl)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril

HRID 11582

反応式

HRID 11582 の反応式
[C:1]([CH2:4][N:5]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH:16][C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([Cl:28])=[CH:23][CH:22]=3)=[O:18])[C:6]1=[O:7])(O)=[O:2].Cl.C(OCC)(=O)C>B.O1CCCC1>[OH:2][CH2:1][CH2:4][N:5]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9][C@H:8]([NH:16][C:17]([C:19]2[NH:20][C:21]3[C:26]([CH:27]=2)=[CH:25][C:24]([Cl:28])=[CH:23][CH:22]=3)=[O:18])[C:6]1=[O:7]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 69195122(S)-1-carboxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril

生成物 1

HCID 69194918(s)-1-(2-Hydroxyethyl)-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril収率 19%

試薬・触媒・溶媒 2

HCID 6331Borane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
35 °C

実験手順

A mixture of (S)-1-carboxymethyl-3-(5-chloroindole-2-carbonylamino)-3,4-dihydrocarbostyril (Example 10) (6 mg) in 1.0 M borane in tetrahydrofuran solution (2 mL) under argon was stirred at 35° C. for 3 h. After cooling to room temperature, 1.0 M aqueous hydrochloric acid (10 mL) and ethyl acetate (10 mL) were added. This mixture was stirred for 3 h before the layers were separated. The organic phase was washed with water (10 mL three times) and evaporated under vacuum. The residue was chromatographed on reverse phase preparative HPLC to isolate the title compound (1.1 mg) and the over-reduction product (S)-1-(2-hydroxyethyl)-3-(5-chloroindole-2-carbonylamino)-1,2,3,4-tetrahydroquinoline (0.9 mg). Title compound HPLC/MS [M+H]+, 384.

後処理

  1. temperatureAfter cooling to room temperature
  2. stirringThis mixture was stirred for 3 h before the layers
  3. customwere separated
  4. washThe organic phase was washed with water (10 mL three times)
  5. customevaporated under vacuum
  6. customThe residue was chromatographed on reverse phase preparative HPLC

出典と根拠

ORDレコード
ord-53c7f65f8f8a484284f4f588533f0f5f
出典データセット
uspto-grants-2006_08
特許番号
US07098235B2

関連ノート

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