p-Toluenesulfonic acid → Ethyl 2-((2-aminoethyl)((2-(trimethylsilyl)ethoxy)carbonyl)amino)acetate para-toluene sulphonate

HRID 1777975Notes

Reaction equation

HRID 1777975 reaction equation
C(OC([NH:8][CH2:9][CH2:10][N:11]([C:18]([O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])=[O:19])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])=O)(C)(C)C.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([OH:36])(=[O:35])=[O:34])=[CH:29][CH:28]=1>CCOCC.CCO>[C:27]1([CH3:37])[CH:28]=[CH:29][C:30]([S:33]([OH:36])(=[O:34])=[O:35])=[CH:31][CH:32]=1.[NH2:8][CH2:9][CH2:10][N:11]([C:18]([O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:26])[CH3:25])=[O:19])[CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 131734793Ethyl 2-((2-((tert-butoxycarbonyl)amino)ethyl)((2-(trimethylsilyl)ethoxy)carbonyl)amino)acetate2×

Product 1

HCID 131734791Ethyl 2-((2-aminoethyl)((2-(trimethylsilyl)ethoxy)carbonyl)amino)acetate para-toluene sulphonate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of ethyl 2-((2-((tert-butoxycarbonyl)amino)ethyl)((2-(trimethylsilyl)ethoxy)carbonyl)amino)acetate (intermediate 125, 7.70 g, 19.72 mmol) in Et2O (50 ml) was added to a solution of para-toluene sulphonic acid (3.94 g, 20.70 mmol) in EtOH (50 ml) at room temperature. The rotated solution was then evaporated under a reduced pressure of 270 mbar at room temperature for 40 minutes and then for 1 h at 55° C. To the residue was added EtOH (50 ml), which was again removed by evaporation to give the title compound as a yellow oil. (MS) ESI-MS 291.3 [M+H]+

Workup

  1. customThe rotated solution was then evaporated under a reduced pressure of 270 mbar at room temperature for 40 minutes
  2. additionTo the residue was added EtOH (50 ml), which
  3. customwas again removed by evaporation

Sources & evidence

ORD record
ord-bf6ea6978a4a4b73bd829cfa618deebc
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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