Water → HCID 90281961, compound

HRID 1497538Notes

Reaction equation

HRID 1497538 reaction equation
[C:1]([O:5][C:6](=[O:44])[CH2:7][N:8]([CH2:30][C:31]1[CH:32]=[C:33]([CH:41]=[CH:42][CH:43]=1)[C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:9][C:10]([N:12]([C:14]1[CH:19]=[CH:18][C:17]([O:20]COCC[Si](C)(C)C)=[CH:16][C:15]=1[Cl:29])[CH3:13])=[O:11])([CH3:4])([CH3:3])[CH3:2].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[C:1]([O:5][C:6](=[O:44])[CH2:7][N:8]([CH2:30][C:31]1[CH:32]=[C:33]([CH:41]=[CH:42][CH:43]=1)[C:34]([O:36][C:37]([CH3:39])([CH3:38])[CH3:40])=[O:35])[CH2:9][C:10]([N:12]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]=1[Cl:29])[CH3:13])=[O:11])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 16028TetrabutylammoniumHCID 90282032HCID 90282032, compound

Product 1

HCID 90281961HCID 90281961, compoundYield 90.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of tert-butyl 3-{[(2-tert-butoxy-2-oxoethyl){2-[(2-chloro-4-{[2-(trimethylsilyl)ethoxy]methoxy}phenyl)(methyl)amino]-2-oxoethyl}amino]methyl}benzoate (805 mg) in tetrahydrofuran (16.1 mL) was added a 1 M solution of tetra-n-butylammonium in tetrahydrofuran (3.72 mL), followed by stirring at 50° C. for 4 days. To a reaction solution was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and 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 tert-butyl 3-{[(2-tert-butoxy-2-oxoethyl){2-[(2-chloro-4-hydroxyphenyl)(methyl)amino]-2-oxoethyl}amino]methyl}benzoate (583 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, then dried 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-fc2a7e990dee4d56ba8c64bf25c5cc03
Source dataset
uspto-grants-2015_12
Patent number
US09199927B2

Reaction notes

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