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Hydrochloric Acid → benzyl {2-(4-bromophenyl)-1-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}carbamate

HRID 1881462
ノート
印刷プレビュー

反応式

HRID 1881462 の反応式
Cl.[CH2:2]([O:9][C:10]([NH:12][CH:13]([C:22]1[N:23](C(OC(C)(C)C)=O)[CH:24]=[C:25]([CH2:27][C:28]([CH3:32])([CH3:31])[CH2:29][CH3:30])[N:26]=1)[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Br:21])=[CH:17][CH:16]=1)=[O:11])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:47][N:48]([CH3:53])[S:49](Cl)(=[O:51])=[O:50]>CO.C(Cl)Cl.O>[Br:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][CH:13]([NH:12][C:10](=[O:11])[O:9][CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:22]2[N:23]([S:49]([N:48]([CH3:53])[CH3:47])(=[O:51])=[O:50])[CH:24]=[C:25]([CH2:27][C:28]([CH3:31])([CH3:32])[CH2:29][CH3:30])[N:26]=2)=[CH:20][CH:19]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 83372Dimethylsulphamoyl chlorideHCID 66705603tert-butyl 2-[1-{[(benzyloxy)carbonyl]amino}-2-(4-bromophenyl)ethyl]-4-(2,2-dimethylbutyl)-1H-imidazole-1-carboxylate

生成物 1

HCID 86637798benzyl {2-(4-bromophenyl)-1-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}carbamate

試薬・触媒・溶媒

3
HCID 887Methanol溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
70 °C

実験手順

Hydrogen chloride (4 M in 1,4-dioxane) (2 mL, 8 mmol) was added to an ambient temperature solution of tert-butyl 2-[1-{[(benzyloxy)carbonyl]amino}-2-(4-bromophenyl)ethyl]-4-(2,2-dimethylbutyl)-1H-imidazole-1-carboxylate (for synthesis see Example 37) (600 mg, 1.03 mmol) in methanol (4 mL). After stirring at 70° C. for 1 h, volatiles were removed in vacuo. The residue was partitioned between methanol/ethyl acetate and 10% aqueous sodium hydroxide. The aqueous phase was extracted with ethyl acetate. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo. Triethylamine (0.43 mL, 3.09 mmol) followed by dimethylsulfamoyl chloride (0.22 mL, 2.06 mmol) were added to an ambient temperature solution of the crude residue in methylene chloride (10 mL). After stirring at ambient temperature overnight, the reaction mixture was diluted with water and extracted with ethyl acetate and methylene chloride. The combined organic extracts were dried (magnesium sulfate) and concentrated in vacuo to afford benzyl {2-(4-bromophenyl)-1-[1-[(dimethylamino)sulfonyl]-4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]ethyl}carbamate which was used in the subsequent step without further purification.

後処理

  1. customvolatiles were removed in vacuo
  2. customThe residue was partitioned between methanol/ethyl acetate and 10% aqueous sodium hydroxide
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  5. concentrationconcentrated in vacuo
  6. stirringAfter stirring at ambient temperature overnight
  7. extractionextracted with ethyl acetate and methylene chloride
  8. dry with materialThe combined organic extracts were dried (magnesium sulfate)
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b6ad0f0ed7f044a8975b557853364d09
出典データセット
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08318767B2

反応ノート

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