Dimethyl Sulfoxide → HCID 69103452, compound

HRID 2220393Notes

Reaction equation

HRID 2220393 reaction equation
CC1C=CC(S(O[CH2:12][C@@H:13]([C:22]2[CH:23]=[N:24][C:25]([NH:28][C:29](=[O:31])[CH3:30])=[CH:26][CH:27]=2)[O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])(=O)=O)=CC=1.[Br:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][NH2:41])=[CH:35][CH:34]=1.CS(C)=O.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C.O>[Br:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][NH:41][CH2:12][C@@H:13]([C:22]2[CH:27]=[CH:26][C:25]([NH:28][C:29](=[O:31])[CH3:30])=[N:24][CH:23]=2)[O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:16])[CH3:17])=[CH:35][CH:34]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 533915p-BromophenethylamineHCID 9804510HCID 9804510, compound

Product 1

HCID 69103452HCID 69103452, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of (2R)-2-[6-(acetylamino)-3-pyridyl]-2-[[tert-butyl(dimethyl)silyl]oxy]ethyl 4-methylbenzenesulfonate (3.50 g), (2-(4-bromophenyl)ethyl]-amine (3.01 g) and dimethyl sulfoxide (1.75 ml) was added N,N-diisopropylethylamine (1.31 ml) and the mixture was stirred at 80° C. for 24 hours. After cooling to room temperature, the mixture was diluted with ethyl acetate (35 ml) and water (35 ml), and the organic layer was separated. The organic layer was washed with water (35 ml×2) and brine (35 ml), and dried over magnesium sulfate. Filtration followed by evaporation gave a yellow paste (5.36 g) which was chromatographed on silica gel (eluent: hexane/ethyl acetate) to give N-[5-[(1R)-2-[[2-(4-bromophenyl)ethyl]-amino]-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl]-2-pyridyl]acetamide (3.33 g) as a colorless paste.

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe organic layer was separated
  3. washThe organic layer was washed with water (35 ml×2) and brine (35 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationFiltration
  6. customfollowed by evaporation
  7. customgave a yellow paste (5.36 g) which
  8. customwas chromatographed on silica gel (eluent: hexane/ethyl acetate)

Sources & evidence

ORD record
ord-c251cd55d489487589cb95a191c75e93
Source dataset
uspto-grants-2008_08
Patent number
US07417060B2

Reaction notes

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