1-Phenethylamine, (-)- → (s)-6-Chloro-1,2-dihydro-2-(trifluoromethyl)-3-quinolinecarboxylic acid

HRID 722353ノート

反応式

HRID 722353 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]([F:15])([F:14])[F:13])[C:6]([C:16]([OH:18])=[O:17])=[CH:5]2.C[C@H](N)C1C=CC=CC=1>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C@H:7]([C:12]([F:15])([F:13])[F:14])[C:6]([C:16]([OH:18])=[O:17])=[CH:5]2

参加物

4

反応物 2

HCID 758181-Phenethylamine, (-)-HCID 100163706-Chloro-1,2-dihydro-2-(trifluoromethyl)-3-quinolinecarboxylic acid

生成物 1

HCID 9878729(s)-6-Chloro-1,2-dihydro-2-(trifluoromethyl)-3-quinolinecarboxylic acid

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 6-chloro-1,2-dihydro-2-(trifluoromethyl)-3-quinolinecarboxylic acid (Example 157) (6.75 g, 24.3 mmol) in ethyl acetate (25 mL) was added (S)-(−)-α-methylbenzylamine (1.50 g, 12.2 mmol). To the resulting solution was added hexanes (50 mL) with mixing. Stirring was discontinued and the reaction held static at room temperature for 16 hours during which time yellow crystals formed. The crystals were collected and washed with ethyl acetate-hexanes (100 mL, 1:2). The resulting yellow solid (932 mg) was dissolved in ethyl acetate (20 mL) and extracted with 1 N HCl (3×10 mL). The organic layer was dried over sodium sulfate and solvent removed at reduced pressure. The (s)-6-chloro-1,2-dihydro-2-(trifluoromethyl)-3-quinolinecarboxylic acid was obtained as a yellow solid (648 mg, 10% yield). mp 173–176° C. 1H NMR (acetone-d6, 300 MHz) 7.80 (s, 1H), 7.35 (d, 1H, J=2.2 Hz), 7.18 (d, 1H, J=8.0, J=2.2 Hz), 6.86 (d, 1H, J=8.0 Hz), 6.60 (brs, 1H), 5.20 (m, 1H). Anal. Calc'd. for C11H7NO2F3Cl C, 47.40 H, 2.54; N, 5.40. Found C, 47.49; H, 2.60; N, 4.98. The compound was determined to have an optical purity greater than 90% ee. Optical purity was determined by HPLC as described in Example 66.

後処理

  1. additionwith mixing
  2. customformed
  3. customThe crystals were collected
  4. washwashed with ethyl acetate-hexanes (100 mL, 1:2)
  5. dissolutionThe resulting yellow solid (932 mg) was dissolved in ethyl acetate (20 mL)
  6. extractionextracted with 1 N HCl (3×10 mL)
  7. dry with materialThe organic layer was dried over sodium sulfate and solvent
  8. customremoved at reduced pressure

出典と根拠

ORDレコード
ord-22658fbd29d949538de2b767ff16846a
出典データセット
uspto-grants-2006_11
特許番号
US07138411B2

反応ノート

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