Trimethylsilyl iodide → N-[2-hydroxy-5-((1R)-1-hydroxy-2-{[4-({[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethyl]amino}ethyl)phenyl]methanesulfonamide

HRID 990084Notes

Reaction equation

HRID 990084 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:43][Si](CC)(CC)CC)[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH2:29][C:30]3[N:34]=[C:33]([C:35]4[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=4)[O:32][N:31]=3)(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[CH:11][C:10]=1[NH:51][S:52]([CH3:55])(=[O:54])=[O:53])C1C=CC=CC=1.C[Si](I)(C)C.S(=O)(=O)(O)[O-].[Na+]>C(#N)C>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:43])[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([S:26]([CH2:29][C:30]3[N:34]=[C:33]([C:35]4[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=4)[O:32][N:31]=3)(=[O:27])=[O:28])=[CH:24][CH:25]=2)=[CH:11][C:10]=1[NH:51][S:52]([CH3:55])(=[O:53])=[O:54]

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 516919Sodium BisulfateHCID 12044212N-(2-(benzyloxy)-5-{(1R)-2-{[4-({[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethyl]amino}-1-[(triethylsilyl)oxy]ethyl}phenyl)methanesulfonamide

Product 1

HCID 9830193N-[2-hydroxy-5-((1R)-1-hydroxy-2-{[4-({[5-(4-methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethyl]amino}ethyl)phenyl]methanesulfonamideYield 64.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the O-protected amino alcohol of Example 26 (0.292 g, 0.362 mmol) in acetonitrile (3 mL) was added 5 equivalents of trimethylsilyl iodide (0.26 mL, 0.1.81 mmol). The reaction mixture was heated to 50° C. for 16 h. TLC shows the absence of starting material, so 1 mL of dilute aqueous sodium bisulfate (Na2S2O5) solution was added to the room temperature reaction mixture and it was stirred vigorously for 15 minutes. The reaction mixture was evaporated in vacuo to dryness and the residue was flash chromatographed (silica gel; dichloromethane/chloroform/methanol: 12/3/2) to afford 0.140 g of the title compound as a light yellow crystalline solid.

Workup

  1. additionwas added to the room temperature reaction mixture and it
  2. customThe reaction mixture was evaporated in vacuo to dryness
  3. customchromatographed (silica gel; dichloromethane/chloroform/methanol: 12/3/2)

Sources & evidence

ORD record
ord-25000a142f8c4d3cbb3300e2675e96bf
Source dataset
uspto-grants-2002_10
Patent number
US06458817B1

Reaction notes

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