p-Toluenesulfonic acid → tert-butyl N-[(1R)-1-(benzylcarbamoyl)-2-hydroxyethyl]carbamate

HRID 1844769Notes

Reaction equation

HRID 1844769 reaction equation
[CH2:1]([NH:8][C:9](=[O:27])[CH:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:11][O:12][C@@H]1CCCCO1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C>[CH2:1]([NH:8][C:9](=[O:27])[C@H:10]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:25])[CH3:24])[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 86650906HCID 86650906, compound

Product 1

HCID 46223140tert-butyl N-[(1R)-1-(benzylcarbamoyl)-2-hydroxyethyl]carbamateYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 12.86 g of Intermediate 3 and 0.65 g of p-toluensulfonic acid in 100 mL of ethanol was heated at reflux temperature for 2 hours. The solvent was evaporated under vacuum and to the residue was added ethyl acetate (100 mL) which resulted in the precipitation of a white solid. The solvent was partially distilled and 150 mL of petroleum oil was added and stirred overnight. The solid was collected by filtration and dried yielding 6.5 g of the title compound as a white solid.

Workup

  1. temperatureat reflux temperature for 2 hours
  2. customThe solvent was evaporated under vacuum and to the residue
  3. additionwas added ethyl acetate (100 mL) which
  4. customresulted in the precipitation of a white solid
  5. distillationThe solvent was partially distilled
  6. addition150 mL of petroleum oil was added
  7. filtrationThe solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-e9d560bf5ea04961ab15414ac1485979
Source dataset
uspto-grants-2015_02
Patent number
US08946477B2

Reaction notes

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