Water → HCID 86686409, compound

HRID 2167417Notes

Reaction equation

HRID 2167417 reaction equation
CS(O[CH2:6][CH2:7][CH2:8][N:9]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:10][C@@H:11]([NH:13][C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH3:12])(=O)=O.[H-].[Na+].O>CS(C)=O>[CH3:12][C@H:11]1[CH2:10][N:9]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:8][CH2:7][CH2:6][N:13]1[C:14]([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15]

Participants

5

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 86686408HCID 86686408, compound

Product 1

HCID 86686409HCID 86686409, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (S)-6-Benzyloxycarbonylamino-4-(tert-butoxycarbonyl)-4-azaheptyl methanesulfonate (425 g, 0.956 mol) in dimethyl sulfoxide (1.6 L) was added 60% sodium hydride (76.5 g, 1.91 mol) at an internal temperature of 25° C. or below, followed by stirring at room temperature for 2 hours. After confirming the disappearance of the starting materials by TLC, the reaction mixture was poured into water, followed by extracting with ethyl acetate. The resulting organic layer was washed with saturated brine, 0.5 N hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine in this order, and then dried over anhydrous sodium sulfate. The resulting solution was filtered and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography (14% ethyl acetate-petroleum ether) to give the target product as a pale yellow oil (199 g, containing about 30 g of mineral oil, yield 50.4%).

Workup

  1. extractionby extracting with ethyl acetate
  2. washThe resulting organic layer was washed with saturated brine, 0.5 N hydrochloric acid, saturated aqueous sodium bicarbonate, and saturated brine in this order
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationThe resulting solution was filtered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash silica gel chromatography (14% ethyl acetate-petroleum ether)

Sources & evidence

ORD record
ord-31cdd498e92142dd9b07d85682d42978
Source dataset
uspto-grants-2015_06
Patent number
US09045460B2

Reaction notes

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