Methanol → 2,6-dichloro-4-[[[(1R)-1-(1-naphthalenyl)ethyl]amino]carbonyl]benzoic acid

HRID 1352031ノート

反応式

HRID 1352031 の反応式
[OH-].[Na+].[Cl:3][C:4]1[CH:13]=[C:12]([C:14]([NH:16][C@@H:17]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)[CH3:18])=[O:15])[CH:11]=[C:10]([Cl:29])[C:5]=1[C:6]([O:8]C)=[O:7].N1CC2C(=CC=CC=2)C[C@H]1C(O)=O.CO>O.O1CCCC1>[Cl:3][C:4]1[CH:13]=[C:12]([C:14]([NH:16][C@@H:17]([C:19]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21][CH:20]=2)[CH3:18])=[O:15])[CH:11]=[C:10]([Cl:29])[C:5]=1[C:6]([OH:8])=[O:7]

参加物

7

反応物 4

HCID 887MethanolHCID 14798Sodium Hydroxide3 回HCID 2733226(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acidHCID 865851452,6-dichloro-4-[[[(1R)-1-(1-naphthalenyl)ethyl]amino)carbonyl]benzoic acid, methyl ester

生成物 1

HCID 599772642,6-dichloro-4-[[[(1R)-1-(1-naphthalenyl)ethyl]amino]carbonyl]benzoic acid収率 89%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of sodium hydroxide (0.62 g, 15.5 mmol) in water (100 mL) was added to a solution of 2,6-dichloro-4-[[[(1R)-1-(1-naphthalenyl)ethyl]amino]carbonyl]benzoic acid, methyl ester (5.62 g, 14.0 mmol) in tetrahydrofuran (100 mL). The solution was stirred overnight at room temperature. Tic indicated that the reaction was not complete. 1 M NaOH (20 mL) was added and the mixture was heated at reflux for 6 h. Methanol (100 mL) was added and the mixture was stirred overnight at room temperature. Again, tic indicated that the reaction was not complete so the reaction mixture was heated at reflux for 2 h, 1 M NaOH (100 mL) was added and the solution was heated at reflux for a further 4 h. The reaction mixture was allowed to stand overnight at room temperature, then the solvent was evaporated, and water (100 mL) and 1 M HCl (200 mL) were added. The mixture was stirred for 20 min and then the white solid was filtered off and dried overnight in a vacuum oven (25 mm Hg, 60° C.) to give 2,6-dichloro-4-[[[(1R)-1-(1-naphthalenyl)ethyl]amino]carbonyl]benzoic acid (4.84 g, 89%) as a white solid, mp 213–215° C. (dec.).

後処理

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 6 h
  3. stirringthe mixture was stirred overnight at room temperature
  4. temperaturewas heated
  5. temperatureat reflux for 2 h
  6. temperaturethe solution was heated
  7. temperatureat reflux for a further 4 h
  8. waitto stand overnight at room temperature
  9. customthe solvent was evaporated
  10. additionwater (100 mL) and 1 M HCl (200 mL) were added
  11. stirringThe mixture was stirred for 20 min
  12. filtrationthe white solid was filtered off
  13. customdried overnight in a vacuum oven (25 mm Hg, 60° C.)

出典と根拠

ORDレコード
ord-669c8e6af4b3411a8243447ed093613c
出典データセット
uspto-grants-2007_05
特許番号
US07217728B2

反応ノート

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