2-Methylbenzenesulfonic acid hydrate → HCID 67189722, compound

HRID 2355343Notes

Reaction equation

HRID 2355343 reaction equation
O.C1(C)C(S(O)(=O)=O)=CC=CC=1.C(OC([NH:20][C@@H:21]([CH2:37][CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1)[CH2:22][N:23]([CH2:33][CH2:34][CH2:35][CH3:36])[C:24]([O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])=[O:25])=O)(C)(C)C>CCO.CCOCC>[NH2:20][C@@H:21]([CH2:37][CH:38]1[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]1)[CH2:22][N:23]([CH2:33][CH2:34][CH2:35][CH3:36])[C:24]([O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:30])[CH3:31])=[O:25]

Participants

5

Reactant 2

HCID 124969952-Methylbenzenesulfonic acid hydrateHCID 67190138HCID 67190138, compound

Product 1

HCID 67189722HCID 67189722, compoundYield 151.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of toluenesulfonic acid monohydrate (199.4 mg, 1.0 mmol) in absolute EtOH (1.0 mL) was added to a solution of (2S)-2-(tert-butoxycarbonylamino)-1-(N-butyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-3-cyclohexylpropane (468.5 mg, 1.03 mmol) in Et2O (10 mL). This solution was placed in a flask on a rotary evaporator and the Et2O was removed at rt. The flask was then lowered into the water bath (temperature: 60° C.) and the selective removal of the Boc group proceeded concurrently with removal of the remainder of solvent to afford (2S)-2-amino-1-(N-butyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)-3-cyclohexylpropane (556.7 mg, 98%) as a white solid.

Workup

  1. customThis solution was placed in a flask on a rotary evaporator
  2. customthe Et2O was removed at rt
  3. customwas then lowered into the water bath (temperature: 60° C.)
  4. customthe selective removal of the Boc group
  5. customproceeded concurrently with removal of the remainder of solvent

Sources & evidence

ORD record
ord-f47be234522049d281d4ca91beb23007
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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