Iodine → HCID 178455621, compound

HRID 2294705Notes

Reaction equation

HRID 2294705 reaction equation
[I:1]I.[OH-].[Na+].[C:5]([S:9]([CH2:12][C@@H:13]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:14]([NH:16][C@@H:17]([CH2:36][C:37]1[N:38]=[CH:39][NH:40][CH:41]=1)[C:18]([NH:20][C@@H:21]([CH2:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[C@@H:22]([OH:28])[C@H:23]([CH:25]1[CH2:27][CH2:26]1)[OH:24])=[O:19])=[O:15])(=[O:11])=[O:10])([CH3:8])([CH3:7])[CH3:6]>CO.O>[C:5]([S:9]([CH2:12][C@@H:13]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:14]([NH:16][C@@H:17]([CH2:36][C:37]1[N:38]=[CH:39][NH:40][C:41]=1[I:1])[C:18]([NH:20][C@@H:21]([CH2:29][CH:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)[C@@H:22]([OH:28])[C@H:23]([CH:25]1[CH2:26][CH2:27]1)[OH:24])=[O:19])=[O:15])(=[O:11])=[O:10])([CH3:8])([CH3:6])[CH3:7]

Participants

6

Reactant 3

HCID 807IodineHCID 14798Sodium Hydroxide2×HCID 178455612HCID 178455612, compound

Product 1

HCID 178455621HCID 178455621, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

10.4 ml (2.08 mmol) of a 0.2N methanolic iodine solution and 2.4 ml (0.48 mmol) of 0.2N sodium hydroxide solution are simultaneously added dropwise at 0° while stirring to a mixture of 630 mg (1 mmol) of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]imidazole-4-propionamide and 20 ml (4 mmol) of 0.2N sodium hydroxide solution in 20 ml of methanol. The colourless reaction mixture is stirred at 0° for 5 minutes and thereafter at room temperature for 2.5 hours. Subsequently, the mixture is diluted with 25 ml of water and extracted twice with 80 ml of ethyl acetate each time. The combined organic phases are washed with saturated sodium chloride solution, dried over sodium sulphate and evaporated under reduced pressure. For purification, the residue (750 mg) is chromatographed using a 15:1 mixture of methylene chloride and methanol as the eluent. There are obtained 504 mg of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-5-iodoimidazole-4-propionamide, MS: 757 (M+H)+, and 38 mg of (S)-α-[(S)-α-[(tert-butylsulphonyl)methyl]hydrocinnamamido]-N-[(1S,2R,3S)-1-(cyclohexylmethyl)-3-cyclopropyl-2,3-dihydroxypropyl]-2,5-iodoimidazole-4-propionamide, MS: 883 (M+H)+, each as a colourless solid.

Workup

  1. waitat room temperature for 2.5 hours
  2. extractionextracted twice with 80 ml of ethyl acetate each time
  3. washThe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialdried over sodium sulphate
  5. customevaporated under reduced pressure
  6. customFor purification
  7. customthe residue (750 mg) is chromatographed
  8. additiona 15:1 mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-2a7e1b2685d443b3b8950057e7bf3868
Source dataset
uspto-grants-1997_11
Patent number
US05688946

Reaction notes

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