Water → {3-[2-(tert-Butyl-dimethyl-silanyloxy)-1-(2-methoxy-ethylamino)-ethyl]-phenyl}-carbamic acid benzyl ester

HRID 221407Notes

Reaction equation

HRID 221407 reaction equation
CS(O[CH:6]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH:17]=1)[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])(=O)=O.[CH3:33][O:34][CH2:35][CH2:36][NH2:37].O>C1COCC1>[CH2:26]([O:25][C:23](=[O:24])[NH:22][C:18]1[CH:19]=[CH:20][CH:21]=[C:16]([CH:6]([NH:37][CH2:36][CH2:35][O:34][CH3:33])[CH2:7][O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH:17]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 80182-MethoxyethylamineHCID 866562641-(3-(Benzyloxycarbonylamino)phenyl)-2-(tert-butyldimethylsilyloxy)ethyl methanesulfonate

Product 1

HCID 67329562{3-[2-(tert-Butyl-dimethyl-silanyloxy)-1-(2-methoxy-ethylamino)-ethyl]-phenyl}-carbamic acid benzyl esterYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

1-(3-(Benzyloxycarbonylamino)phenyl)-2-(tert-butyldimethylsilyloxy)ethyl methanesulfonate (3.5 g) was dissolved in dry THF (10 mL) and methoxyethylamine (5.4 g) was added in a sealed tube and heated to 70° C. for 16 hours. Water was added and the reaction mixture extracted with DCM (2×20 mL). The organic phase was separated, dried over Na2SO4 and concentrated to give the crude product, which was purified by column chromatography to give the title compound (1 g, 30%).

Workup

  1. extractionthe reaction mixture extracted with DCM (2×20 mL)
  2. customThe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customto give the crude product, which
  6. customwas purified by column chromatography

Sources & evidence

ORD record
ord-e9fc3d3235594f4d82e3240deeefba30
Source dataset
uspto-grants-2012_06
Patent number
US08207167B2

Reaction notes

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