HCID 68157391, compound → HCID 68157654, compound

HRID 242937Notes

Reaction equation

HRID 242937 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:10](=O)[NH:11][C:12]1[C:13]([NH:18][C:19]2[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=2)=[N:14][CH:15]=[CH:16][CH:17]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]>CC(O)=O>[C:1]([O:5][C:6](=[O:27])[NH:7][C@H:8]([C:10]1[N:18]([C:19]2[CH:20]=[C:21]([CH3:25])[CH:22]=[CH:23][CH:24]=2)[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[N:11]=1)[CH3:9])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 68157391HCID 68157391, compound

Product 1

HCID 68157654HCID 68157654, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of [(S)-1-(2-m-tolylaminopyridin-3-ylcarbamoyl)ethyl]carbamic acid tert-butyl ester (3.01 mmol) in AcOH (20 mL) was heated at 70° C. for 2 h under a nitrogen atmosphere. After cooling to RT, the volatiles were removed in vacuo and the resulting residue partitioned between DCM and a saturated aqueous solution of NaHCO3. The aqueous phase was extracted with DCM (×3) and the combined organic fractions washed with water, dried (Na2SO4) and concentrated in vacuo to afford the title compound as an off-white foam (quantitative). LCMS (Method C): RT 3.23 min [M+H]+ 353.4.

Workup

  1. customthe volatiles were removed in vacuo
  2. customthe resulting residue partitioned between DCM
  3. extractionThe aqueous phase was extracted with DCM (×3)
  4. washthe combined organic fractions washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e7e9dd9c9e06461e8a4a090820625460
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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