p-Toluenesulfonic acid → HCID 67189820, compound

HRID 2355451Notes

Reaction equation

HRID 2355451 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.C(OC([NH:19][C@H:20]([CH2:28][N:29]([CH3:39])[C:30]([O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=[O:31])[C@@H:21]([CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[OH:22])=O)(C)(C)C>CCO.CCOCC>[NH2:19][C@H:20]([CH2:28][N:29]([CH3:39])[C:30]([O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])=[O:31])[C@@H:21]([CH:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1)[OH:22]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 67190531HCID 67190531, compound

Product 1

HCID 67189820HCID 67189820, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of TsOH (36.8 mg, 0.194 mg) in 1.0 mL EtOH (1 mL) was added to (1R,2R)-2-(t-butoxycarbonylamino)-1-cyclopentyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)-amino)propan-1-ol (68.2 mg, 0.164 mmol) in 3.0 mL Et2O (3 mL). The solvent was removed under reduced pressure at 60° C. and the residue maintained at this temperature for 1 h. The residue was taken up into CH2Cl2 (50 mL), washed with 1 N aq NaOH and brine, and dried over Na2SO4. Removal of the solvent left (1R,2R)-2-amino-1-cyclopentyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-1-ol which was used without purification.

Workup

  1. customThe solvent was removed under reduced pressure at 60° C.
  2. temperaturethe residue maintained at this temperature for 1 h
  3. washwashed with 1 N aq NaOH and brine
  4. dry with materialdried over Na2SO4
  5. customRemoval of the solvent
  6. waitleft (1R,2R)-2-amino-1-cyclopentyl-3-(N-methyl-N-(2-(trimethylsilyl)ethoxycarbonyl)amino)propan-1-ol which
  7. customwas used without purification

Sources & evidence

ORD record
ord-2780dbf3bd3a4a91bdb8f4f4553b4a81
Source dataset
uspto-grants-2010_07
Patent number
US07754737B2

Reaction notes

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