Citric Acid → HCID 66955114, compound

HRID 1697875Notes

Reaction equation

HRID 1697875 reaction equation
[CH2:1]([O:8][C:9](Cl)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]([O:16][C:17](=[O:33])[NH:18][C:19]1[CH:24]=[C:23]([C:25]2[CH:29]=[C:28]([CH3:30])[NH:27][N:26]=2)[C:22]([F:31])=[CH:21][C:20]=1[CH3:32])([CH3:15])([CH3:14])[CH3:13].CCN(C(C)C)C(C)C.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[CH2:1]([O:8][C:9]([N:27]1[C:28]([CH3:30])=[CH:29][CH:25]([C:23]2[CH:24]=[C:19]([NH:18][C:17]([O:16][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:33])[C:20]([CH3:32])=[CH:21][C:22]=2[F:31])[NH:26]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 66955181HCID 66955181, compound

Product 1

HCID 66955114HCID 66955114, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzylchloroformate (104 mg) was added dropwise to a room temperature solution of [4-fluoro-2-methyl-5-(5-methyl-1H-pyrazol-3-yl)-phenyl]-carbamic acid tert-butyl ester and DIPEA in CH2Cl2 (2 ml). The mixture was stirred at room temperature for one hour, and then 10% aqueous citric acid solution was added. The organic layer was separated dried (Na2SO4), filtered and concentrated under reduced pressure. “Flash chromatography” of the residue (0 to 20% EtOAc in hexanes) gave 210 mg of 3-(5-tert-Butoxycarbonylamino-2-fluoro-4-methyl-phenyl)-5-methyl-2H-pyrazole-1-carboxylic acid benzyl ester as a white solid.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-831a08757d334114a1988c50359ee7dd
Source dataset
uspto-grants-2012_04
Patent number
US08163929B2

Reaction notes

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