Water → HCID 15284069, compound

HRID 2268726Notes

Reaction equation

HRID 2268726 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:13][CH3:14])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.O>C1COCC1>[CH2:13]([N:12]([C:15]([O:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:11][CH2:10][CH2:9][OH:8])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 57152513HCID 57152513, compound

Product 1

HCID 15284069HCID 15284069, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-Ethyl 3-benzyloxycarbonylamino-1-propanol t-butyldimethylsilyl ether (8.5 g) was dissolved in THF (120 ml), and to the resulting solution was added under ice-cooling a solution of 1N tetra-butylammonium fluoride in THF (48 ml). The resultant mixture was stirred at room temperature for 1 hour. Ethyl acetate and water were added to the reaction solution obtained. The organic layer so sepasated was washed with water and then dried over magnesium sulfate. The solvent was evaporated off from the solution, and the residue was purified by a silica gel chromatography, thus affording the titled compound (4.0 g; 71%)

Workup

  1. additionto the resulting solution was added under ice-
  2. customobtained
  3. washThe organic layer so sepasated was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was evaporated off from the solution
  6. customthe residue was purified by a silica gel chromatography

Sources & evidence

ORD record
ord-18d9c7d228b54daa9b657fe28e552e1b
Source dataset
uspto-grants-2001_12
Patent number
US06329338B1

Reaction notes

Loading…