Hydrochloric Acid → HCID 90282021, compound

HRID 1497523Notes

Reaction equation

HRID 1497523 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]([NH:13][CH2:14][C:15]1[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=1[C:17]([O:19][CH3:20])=[O:18])=[O:12].Cl[Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].N1C=CN=C1.Cl>CN(C)C=O.O>[Si:26]([O:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:9][CH2:10][C:11]([NH:13][CH2:14][C:15]2[CH:24]=[CH:23][CH:22]=[CH:21][C:16]=2[C:17]([O:19][CH3:20])=[O:18])=[O:12])=[C:2]([Cl:1])[CH:7]=1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 90282076HCID 90282076, compound

Product 1

HCID 90282021HCID 90282021, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-({[3-(2-chloro-4-hydroxyphenyl)propanoyl]amino}methyl)benzoate (380 mg) in N,N-dimethylformamide (4.00 mL) were added chloro tert-butyl dimethylsilane (215 mg) and imidazole (114 mg), followed by stirring at room temperature for 4 hours. To the reaction mixture were added water and 1 M hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, then dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate) to obtain methyl 2-({[3-(4-{[tert-butyl(dimethyl)silyl]oxy}-2-chlorophenyl)propanoyl]amino}methyl)benzoate (500 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-09b1528754f04beb988f74962449f99d
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

Loading…