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

HRID 1352031노트

반응식

HRID 1352031 반응식
[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]

참가 물질

7

반응물 4

HCID 887MethanolHCID 14798Sodium Hydroxide3회HCID 2733226(-)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acidHCID 865851452,6-dichloro-4-[[[(1R)-1-(1-naphthalenyl)ethyl]amino)carbonyl]benzoic acid, methyl ester

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.).

후처리

  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.)

출처 및 근거

ORD 기록
ord-669c8e6af4b3411a8243447ed093613c
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217728B2

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