Hydrochloric Acid → Ethyl 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxylate

HRID 2361273ノート

反応式

HRID 2361273 の反応式
[NH2:1][CH2:2][CH:3]([C:18]1[C:19]([CH3:35])=[C:20]([NH:24][C:25](=[O:34])[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:21]=[CH:22][CH:23]=1)[C:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:10][CH:11]=2)[NH:6][CH:5]=1.O=[CH:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].C1(C)C=CC=CC=1.Cl.O1CCOCC1>C(OCC)(=O)C.C(Cl)Cl>[CH2:27]([O:26][C:25]([NH:24][C:20]1[C:19]([CH3:35])=[C:18]([C:3]2[C:4]3[C:12]4[C:7](=[CH:8][C:9]([O:13][CH2:14][CH2:15][O:16][CH3:17])=[CH:10][CH:11]=4)[NH:6][C:5]=3[C:37]([C:38]([O:40][CH2:41][CH3:42])=[O:39])=[N:1][CH:2]=2)[CH:23]=[CH:22][CH:21]=1)=[O:34])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 312751,4-DioxaneHCID 70211Ethyl oxoacetateHCID 67994818Benzyl 3-(2-amino-1-(6-(2-methoxyethoxy)-1H-indol-3-yl)ethyl)-2-methylphenylcarbamate

生成物 1

HCID 67994870Ethyl 4-(3-(benzyloxycarbonylamino)-2-methylphenyl)-7-(2-methoxyethoxy)-9H-pyrido[3,4-b]indole-1-carboxylate収率 43.8%

試薬・触媒・溶媒 1

HCID 21226138Dichloromethane ethylacetate溶媒

実験手順

To a solution of benzyl 3-(2-amino-1-(6-(2-methoxyethoxy)-1H-indol-3-yl)ethyl)-2-methylphenylcarbamate (0.780 g, 1.647 mmol) and ethyl 2-oxoacetate in toluene (50%) (0.653 mL, 3.29 mmol) at room temperature was added hydrogen chloride in 1,4-dioxane (4.0 M) (0.494 mL, 1.977 mmol). The mixture was stirred room temperature for 16 hr. The volatiles were removed under vacuum. The residue was diluted with water (50 mL), basified with NaHCO3 solution to pH 10, and extracted with ethyl acetate (4×50 mL). The combined extract was washed with brine (40 ml), dried over anhydrous MgSO4, and concentrated to dryness under vacuum. To the residue were added p-xylene (60 mL) and 10% Pd/C (0.46 g), and the mixture was heated at 125° C. under an ambient atmosphere for 4.5 hr. The solid phase was removed by suction filtration. The filtrate was diluted with ethyl acetate (120 ml), washed with brine (40 ml), and dried over anhydrous MgSO4. The desired product (0.399 g, 0.721 mmol, 43.8% yield) was isolated by ISCO (40 g silica gel, solid loading, 15-35% ethyl acetate/CH2Cl2).

後処理

  1. customThe volatiles were removed under vacuum
  2. additionThe residue was diluted with water (50 mL)
  3. extractionextracted with ethyl acetate (4×50 mL)
  4. extractionThe combined extract
  5. washwas washed with brine (40 ml)
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated to dryness under vacuum
  8. additionTo the residue were added p-xylene (60 mL) and 10% Pd/C (0.46 g)
  9. temperaturethe mixture was heated at 125° C. under an ambient atmosphere for 4.5 hr
  10. customThe solid phase was removed by suction filtration
  11. additionThe filtrate was diluted with ethyl acetate (120 ml)
  12. washwashed with brine (40 ml)
  13. dry with materialdried over anhydrous MgSO4

出典と根拠

ORDレコード
ord-e15171e4f7d243c88daecf5070147753
出典データセット
uspto-grants-2014_04
特許番号
US08685969B2

反応ノート

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