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Acetic Acid → N-(2-benzyloxy-5-{1-hydroxy-2-[3-(4-iodo-imidazol-1-yl)-1,1-dimethyl-propylamino]-ethyl}-phenyl)-phenylsulphonamide

HRID 1350919
ノート
印刷プレビュー

反応式

HRID 1350919 の反応式
[I:1][C:2]1[N:3]=[CH:4][N:5]([CH2:7][CH2:8][C:9]([NH2:12])([CH3:11])[CH3:10])[CH:6]=1.[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([OH:33])[CH:28](OCC)O)=[CH:23][C:22]=1[NH:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:37])=[O:36])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[BH4-].[Na+].C(O)(=O)C>C(O)C>[CH2:13]([O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]([OH:33])[CH2:28][NH:12][C:9]([CH3:10])([CH3:11])[CH2:8][CH2:7][N:5]2[CH:6]=[C:2]([I:1])[N:3]=[CH:4]2)=[CH:23][C:22]=1[NH:34][S:35]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)(=[O:36])=[O:37])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][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

6

反応物 4

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 210945453-(4-Iodo-imidazol-1-yl)-1,1-dimethyl-propylamineHCID 21094553n-[2-Benzyloxy-5-(2-ethoxy-1,2-dihydroxy-ethyl)-phenyl]-phenylsulphonamide

生成物 1

HCID 69413237N-(2-benzyloxy-5-{1-hydroxy-2-[3-(4-iodo-imidazol-1-yl)-1,1-dimethyl-propylamino]-ethyl}-phenyl)-phenylsulphonamide収率 69%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

2.1 g (7.7 mmol) of 3-(4-iodimidazol-1-yl)-1,1-dimethyl-propylamine and 3.4 g (7.7 mmol) of N-[2-benzyloxy-5-(2-ethoxy-1,2-dihydroxy-ethyl)-phenyl]-phenylsulphonamide in 25 mL ethanol were refluxed for 18 h. The reaction mixture was cooled to 0° C. and then combined with 0.3 g (7.7 mmol) sodium borohydride. The mixture was stirred for a further 3 h at ambient temperature and then combined with glacial acetic acid. The solvent was removed using the rotary evaporator and the residue was dissolved in 300 mL ethyl acetate/water (1:2). The aqueous phase was made alkaline with conc. ammonia and separated from the organic phase. The organic phase was washed twice with 100 mL water and once with 100 mL of saturated aqueous sodium chloride solution, dried over sodium sulphate and freed from solvent using the rotary evaporator. The residue was purified by flash column chromatography [methylene chloride/methanol/ammonia (90:10:1)]. 3.5 g (5.0 mmol, 69%) N-(2-benzyloxy-5-{1-hydroxy-2-[3-(4-iodo-imidazol-1-yl)-1,1-dimethyl-propylamino]-ethyl}-phenyl)-phenylsulphonamide were obtained as a yellowish solid.

後処理

  1. customThe solvent was removed
  2. customthe rotary evaporator
  3. dissolutionthe residue was dissolved in 300 mL ethyl acetate/water (1:2)
  4. customseparated from the organic phase
  5. washThe organic phase was washed twice with 100 mL water and once with 100 mL of saturated aqueous sodium chloride solution
  6. dry with materialdried over sodium sulphate
  7. customthe rotary evaporator
  8. customThe residue was purified by flash column chromatography [methylene chloride/methanol/ammonia (90:10:1)]

出典と根拠

ORDレコード
ord-5a9081f5c4ac491f89b1b0e016a80474
出典データセット
uspto-grants-2007_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07214698B2

反応ノート

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