Triethylamine → N-(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

HRID 990083Notes

Reaction equation

HRID 990083 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:13][N:12]=[C:11]([CH2:14][S:15]([C:18]3[CH:26]=[CH:25][C:21]([CH2:22][CH2:23][NH2:24])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[N:10]=2)=[CH:5][CH:4]=1.[CH2:27]([O:34][C:35]1[CH:40]=[CH:39][C:38]([CH:41]([O:44][Si:45]([CH2:50][CH3:51])([CH2:48][CH3:49])[CH2:46][CH3:47])[CH2:42]I)=[CH:37][C:36]=1[NH:52][S:53]([CH3:56])(=[O:55])=[O:54])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(N(CC)CC)C>C1COCC1>[CH2:27]([O:34][C:35]1[CH:40]=[CH:39][C:38]([C@@H:41]([O:44][Si:45]([CH2:46][CH3:47])([CH2:48][CH3:49])[CH2:50][CH3:51])[CH2:42][NH:24][CH2:23][CH2:22][C:21]2[CH:20]=[CH:19][C:18]([S:15]([CH2:14][C:11]3[N:10]=[C:9]([C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[O:13][N:12]=3)(=[O:16])=[O:17])=[CH:26][CH:25]=2)=[CH:37][C:36]=1[NH:52][S:53]([CH3:56])(=[O:54])=[O:55])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 120442034-({[5-(4-Methoxyphenyl)-1,2,4-oxadiazol-3-yl]methyl}sulfonyl)phenethylamineHCID 222205844-Benzyloxy-3-(methylsulfonamido)phenyl-1-triethylsiloxy-2-iodoethane

Product 1

HCID 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)methanesulfonamideYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the amine of Example 17 (0.90 g, 1.78 mmol), 1(S)-(4-benzyloxy-3-(methylsulfonamido)phenyl-1-triethylsiloxy-2-iodoethane (0.665 g, 1.60 mmol) and triethylamine (0.50 mL, 3.56 mmol) in THF (4 mL) was heated at 100° C. in a sealed tube for 60 h. The reaction mixture was cooled and evaporated in vacuo. The residue was flash chromatographed (silica gel; dichloromethane/ethyl ether/methanol: 25/25/0.75) to yield 0.740 g of the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customevaporated in vacuo
  3. customchromatographed (silica gel; dichloromethane/ethyl ether/methanol: 25/25/0.75)

Sources & evidence

ORD record
ord-60b6b76d9ae54663acd5014da652bd56
Source dataset
uspto-grants-2002_10
Patent number
US06458817B1

Reaction notes

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