Water → HCID 69202020, compound

HRID 2220656Notes

Reaction equation

HRID 2220656 reaction equation
[Br:1][C:2]1[CH:43]=[CH:42][C:5]([O:6][CH2:7][C:8]([NH:10][CH2:11][C@H:12]([OH:41])[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])=[C:15]([N:28]([S:37]([CH3:40])(=[O:39])=[O:38])[CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[CH:14]=2)=O)=[CH:4][CH:3]=1.N(CCO)(CCO)CCO.O>O1CCCC1>[Br:1][C:2]1[CH:43]=[CH:42][C:5]([O:6][CH2:7][CH2:8][NH:10][CH2:11][C@@H:12]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])=[C:15]([N:28]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[S:37]([CH3:40])(=[O:39])=[O:38])[CH:14]=2)[OH:41])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7618TriethanolamineHCID 69202719HCID 69202719, compound

Product 1

HCID 69202020HCID 69202020, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A 2 mol/L solution of borane dimethylsulfide complex in tetrahydrofuran (1.96 mL) was added dropwise to a solution of 2-(4-bromophenoxy)-N—((R)-2-hydroxy-2-{3-[methanesulfonyl-(2-trimethylsilylethoxymethyl)amino]-4-(2-trimethylsilylethoxymethoxy)phenyl}ethyl)acetamide (1.35 g) in tetrahydrofuran (10 mL) at room temperature under an atmosphere of argon. The mixture was stirred under ref lux for 1.5 hrs, and then cooled to room temperature. A solution of triethanolamine (0.88 g) in tetrahydrofuran (5 mL) was added dropwise to the reaction mixture. After being stirred under reflux for 5 hrs, water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by medium-pressure silica gel column chromatography (eluent: ethyl acetate/ethanol=15/1) to afford the title compound (1.13 g).

Workup

  1. stirringAfter being stirred
  2. temperatureunder reflux for 5 hrs
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by medium-pressure silica gel column chromatography (eluent: ethyl acetate/ethanol=15/1)

Sources & evidence

ORD record
ord-4e3dd16c3424447bb642a3436447f230
Source dataset
uspto-grants-2008_08
Patent number
US07417169B2

Reaction notes

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