Triethylamine → HCID 57260263, compound

HRID 2268724Notes

Reaction equation

HRID 2268724 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][OH:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].C(OCC)(=O)C>C(Cl)Cl.O>[Si:23]([O:15][CH2:14][CH2:13][CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:10])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 562256Benzyl N-(3-hydroxypropyl)carbamate

Product 1

HCID 57260263HCID 57260263, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

3-Benzyloxycarbonylamino-1-propanol (8.1 g) was dissolved in methylene chloride (200 ml), and to the resulting solution were added triethylamine (4.1 g) and t-butyldimethylsilyl chloride (7.1 g). The resultant mixture was stirred at room temperature for 1 day. Ethyl acetate and water were added to the reaction solution obtained. The organic layer so separated was 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 (10.1 g; 82%).

Workup

  1. customobtained
  2. customThe organic layer so separated
  3. dry with materialwas dried over magnesium sulfate
  4. customThe solvent was evaporated off from the solution
  5. customthe residue was purified by a silica gel chromatography

Sources & evidence

ORD record
ord-e2c218e42af64b46bc9ae7c62d02a2c0
Source dataset
uspto-grants-2001_12
Patent number
US06329338B1

Reaction notes

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