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

HRID 1350919Notes

Reaction equation

HRID 1350919 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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)]

Sources & evidence

ORD record
ord-5a9081f5c4ac491f89b1b0e016a80474
Source dataset
uspto-grants-2007_05
Patent number
US07214698B2

Reaction notes

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