p-Toluenesulfonic acid monohydrate → p-Toluenesulfonic acid

HRID 2355370Notes

Reaction equation

HRID 2355370 reaction equation
C(OC(NC[C@@H](N(C(OCC[Si](C)(C)C)=O)CC(N)=O)CC1CCCCC1)=O)(C)(C)C.[CH3:32][C:33]1[CH:34]=[CH:35][C:36]([S:39]([OH:42])(=[O:41])=[O:40])=[CH:37][CH:38]=1.O>CCOCC.C(O)C>[C:33]1([CH3:32])[CH:34]=[CH:35][C:36]([S:39]([OH:42])(=[O:40])=[O:41])=[CH:37][CH:38]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 69471169HCID 69471169, compound

Product 1

HCID 6101p-Toluenesulfonic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
62.5 °C

Procedure

To a solution of above N1-(tert-butoxycarbonyl)-N2-(2-(trimethylsilyl)ethoxycarbonyl)-N2-(aminocarbonylmethyl)-(S)-3-cyclohexylpropane-1,2-diamine in ether (2 mL) was added TsOH.H2O (36.9 mg, 0.22 mmol) in ethanol (1 mL). The resulting solution was put on a rotatory vaporator, ether was removed in vacuum at rt, the bath temperature was raised to 60-65° C., and the mixture was heated in vacuo for 30 min to give (2S)-1-(N-(aminocarbonylmethyl)-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-3-cyclohexylpropyl-2-amine as a p-toluenesulfonic acid salt. MS ESI+ve m/z 358 (M+1).

Workup

  1. customwas removed in vacuum at rt
  2. temperaturethe mixture was heated in vacuo for 30 min

Sources & evidence

ORD record
ord-f8662893ac8948dcbbc9c0a265cac27b
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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