p-Toluenesulfonic acid → HCID 71087221, compound

HRID 927443Notes

Reaction equation

HRID 927443 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:13](=[S:15])[NH2:14])[CH2:9][CH:10]([CH3:12])[CH3:11])(C)(C)C.Br[CH2:18][CH:19]([O:22]C)[O:20]C.[C:24]1(C)C=CC(S(O)(=O)=O)=C[CH:25]=1>C(O)(=O)C>[C:19]([OH:22])(=[O:20])[CH3:18].[CH3:12][CH:10]([CH3:11])[CH2:9][C@@H:8]([C:13]1[S:15][CH:24]=[CH:25][N:14]=1)[NH2:7]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 816722-Bromo-1,1-dimethoxyethaneHCID 54281150HCID 54281150, compound

Product 1

HCID 71087221HCID 71087221, compoundYield 897.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of ((S)-3-methyl-1-thiocarbamoyl-butyl)-carbamic acid tert-butyl ester (1.38 g, 6 mmol), 2-bromo-1,1-dimethoxyethane (CAN:7252-83-7, 1.14 g, 7 mmol) and p-toluene sulfonic acid (50 mg) in acetic acid (20 mL) was stirred at 120° C. for 4. After evaporation of solvents, the residue was diluted with ethyl acetate (20 mL) and water (20 mL). The aqueous phase was washed with ethyl acetate (3×20 mL) and lyophilized to give a brown solid (0.6 g, 63%); MS: m/e 171.1 [M+H+].

Workup

  1. customAfter evaporation of solvents
  2. additionthe residue was diluted with ethyl acetate (20 mL) and water (20 mL)
  3. washThe aqueous phase was washed with ethyl acetate (3×20 mL)

Sources & evidence

ORD record
ord-cae55646963e47b59d826fd1e1a9f1cf
Source dataset
uspto-grants-2016_03
Patent number
US09290451B2

Reaction notes

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