2-Methylbenzenesulfonic acid hydrate → HCID 86626187, compound

HRID 2355344Notes

Reaction equation

HRID 2355344 reaction equation
O.C1(C)C(S(O)(=O)=O)=CC=CC=1.[CH:13]1([CH2:19][C@H:20]([NH:32][CH2:33]C(=O)NC(C)(C)C)[CH2:21][NH:22][C:23](=[O:31])[O:24][CH2:25][CH2:26][Si:27]([CH3:30])([CH3:29])[CH3:28])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C(O)C.CCOCC>[CH:13]1([CH2:19][C@H:20]([NH:32][CH3:33])[CH2:21][NH:22][C:23](=[O:31])[O:24][CH2:25][CH2:26][Si:27]([CH3:29])([CH3:28])[CH3:30])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

5

Reactant 2

HCID 124969952-Methylbenzenesulfonic acid hydrateHCID 86626188HCID 86626188, compound

Product 1

HCID 86626187HCID 86626187, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of toluenesulfonic acid monohydrate (10 mg, 0.053 mmol) in absolute ethanol (1 mL) was added to a solution of 2-(trimethylsilyl)ethyl (S)-3-cyclohexyl-2-((tert-butyl-carbamoyl)methylamino)propylcarbamate (21.3 mg, 0.51 mmol) in Et2O (10 mL). This solution was placed in a flask on a rotary evaporator and the Et2O was removed at ambient temp. The flask was then lowered into a water bath (60° C.) and selective removal of the Boc group proceeded concurrently with removal of the solvent. The reaction was complete within 2 h. This material was taken up in CH2Cl2 (20 mL) and 1N aq NaOH (10 mL) and extracted with CH2Cl2 (2×10 mL). The combined organic layers were washed with brine (2×5 mL), dried over Na2SO4, decanted, and stripped to afford 2-(trimethylsilyl)ethyl (S)-3-cyclohexyl-2-(methylamino)propylcarbamate (15.0 mg, 94%) as a clear film. MS ESI+ve m/z 315 (M+1).

Workup

  1. customThis solution was placed in a flask on a rotary evaporator
  2. customthe Et2O was removed at ambient temp
  3. customThe flask was then lowered into a water bath
  4. custom(60° C.) and selective removal of the Boc group
  5. customproceeded concurrently with removal of the solvent
  6. extraction1N aq NaOH (10 mL) and extracted with CH2Cl2 (2×10 mL)
  7. washThe combined organic layers were washed with brine (2×5 mL)
  8. dry with materialdried over Na2SO4
  9. customdecanted

Sources & evidence

ORD record
ord-f552265ae26940c6931912258ef1c48c
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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