Carbidopa → 2,6-Dimethyl-benzoic acid 5-(2-carboxy-2-hydrazino-propyl)-2-hydroxy-phenyl ester

HRID 2212446Notes

Reaction equation

HRID 2212446 reaction equation
[CH3:1][C@@:2]([NH:15][NH2:16])([C:12]([OH:14])=[O:13])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[C:8]([OH:10])[CH:9]=1.[CH3:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:19]=1[C:20](Cl)=[O:21]>FC(F)(F)C(O)=O>[C:12]([C:2]([NH:15][NH2:16])([CH3:1])[CH2:3][C:4]1[CH:5]=[CH:6][C:7]([OH:11])=[C:8]([O:10][C:20](=[O:21])[C:19]2[C:23]([CH3:27])=[CH:24][CH:25]=[CH:26][C:18]=2[CH3:17])[CH:9]=1)([OH:14])=[O:13]

Participants

4

Reactant 2

HCID 34359CarbidopaHCID 890962,6-Dimethylbenzoyl chloride

Product 1

HCID 695850252,6-Dimethyl-benzoic acid 5-(2-carboxy-2-hydrazino-propyl)-2-hydroxy-phenyl esterYield 15%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of carbidopa (732 mg, 3 mmol) in trifluoroacetic acid (10 mL), was slowly added 2,6-dimethyl-benzoyl chloride (504 mg, 3 mmol) at 0° C. and the mixture stirred at room temperature for 1 h. The reaction mixture was concentrated under reduced pressure. The oily residue was dissolved in acetonitrile/H2O and purified by reverse phase preparative HPLC to afford 196 mg of compound 125 [1H NMR (CD3OD, 400 MHz) 1.49 (s, 3H), 2.45 (d, 6H), 3.10 (dd, 2H), 6.82–7.25 (m, 6H). MS (ESI) m/z 359.23 (M+H+)] and 161 mg of compound 126 [1H NMR (CD3OD, 400 MHz): 1.45 (s, 3H), 2.42 (d, 6H), 3.15 (dd, 2H), 6.74–7.27 (m, 6H). MS (ESI m/z 359.23 (M+H+)].

Workup

  1. customat 0° C.
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe oily residue was dissolved in acetonitrile/H2O
  4. custompurified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-448439f3647b4d159c61e42ec6becb99
Source dataset
uspto-grants-2006_09
Patent number
US07101912B2

Reaction notes

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