Water → Levodopa

HRID 1516942Notes

Reaction equation

HRID 1516942 reaction equation
CC1(C)[O:6][C:5]2[CH:7]=[C:8]([CH2:11][C@H:12]([NH:16]C(OCC3C4C(=CC=CC=4)C4C3=CC=CC=4)=O)[C:13]([OH:15])=[O:14])[CH:9]=[CH:10][C:4]=2[O:3]1.N1CCCCC1.O>C(Cl)Cl.C(O)(C(F)(F)F)=O>[O:14]=[C:13]([C@H:12]([CH2:11][C:8]1[CH:7]=[C:5]([OH:6])[C:4]([OH:3])=[CH:10][CH:9]=1)[NH2:16])[OH:15]

Participants

6

Reactant 3

HCID 962WaterHCID 8082PiperidineHCID 25058854Fmoc-Dopa(acetonide)-OH

Product 1

HCID 6047Levodopa

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To unambiguously determine the chirality of the synthesized Fmoc-DOPA(acetonide)-OH, it was cleaved by 25% piperidine in DCM and TFA/TIS/H2O (95:2.5:2.5) to give a raw free DOPA product, which was subjected to chiral HPLC analysis (CHIROBIOTIC T, Aldrich) using commercially available L- and D/L-DOPA as reference.26 The absence of the D-DOPA peak in the chromatogram confirmed the optical purity of the synthesized Fmoc-DOPA(acetonide)-OH and that L-DOPA retained its chirality under the conditions of refluxing with DMP in the presence of TsOH.27

Sources & evidence

ORD record
ord-b23b79fefd884b81b92b593d227a9dc9
Source dataset
uspto-grants-2012_07
Patent number
US08227628B2

Reaction notes

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