Methanol → HCID 57215122, compound

HRID 741717Notes

Reaction equation

HRID 741717 reaction equation
C(OC([NH:8][C@@H:9]([CH2:14][CH2:15][C:16](=[O:24])[NH:17][C:18]1[N:19]([CH3:23])[CH:20]=[CH:21][N:22]=1)[C:10]([O:12]C)=[O:11])=O)(C)(C)C.FC(F)(F)C(O)=O.CO.C1(C)C=CC=CC=1>ClCCl>[NH2:8][C@@H:9]([CH2:14][CH2:15][C:16](=[O:24])[NH:17][C:18]1[N:19]([CH3:23])[CH:20]=[CH:21][N:22]=1)[C:10]([OH:12])=[O:11]

Participants

6

Reactant 4

HCID 887MethanolHCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57222498HCID 57222498, compound

Product 1

HCID 57215122HCID 57215122, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl (2S)-2-t-butoxycarbonylamino-4-[(1-methylimidazol-2-yl)carbamoyl]butyrate (341 mg) was dissolved in dichloromethane (5 ml), and trifluoroacetic acid (1 ml) was added. The mixture was stirred at room temperature for 2 hours. Methanol and toluene were added, and then the solvents were evaporated under reduced pressure. The resulting residue was dissolved in water (4 ml), and 1N sodium hydroxide (4 ml) was added. The mixture was stirred at room temperature for 3 hours and neutralized by adding 1N hydrochloric acid. The solvent was evaporated under reduced pressure to precipitate colorless needles. The needles were separated by filtration, washed successively with water, methanol and ether, and dried to give the title compound (72 mg).

Workup

  1. customthe solvents were evaporated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in water (4 ml)
  3. addition1N sodium hydroxide (4 ml) was added
  4. stirringThe mixture was stirred at room temperature for 3 hours
  5. additionby adding 1N hydrochloric acid
  6. customThe solvent was evaporated under reduced pressure
  7. customto precipitate colorless needles
  8. customThe needles were separated by filtration
  9. washwashed successively with water, methanol and ether
  10. customdried

Sources & evidence

ORD record
ord-57d3af52fdbb4c70ad6fffd0e36be3d1
Source dataset
uspto-grants-1996_09
Patent number
US05552427

Reaction notes

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