Boc-L-Valine → Tert-butoxycarbonylalanine

HRID 1376476Notes

Reaction equation

HRID 1376476 reaction equation
C[CH:2]([C@H:4]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:5]([OH:7])=[O:6])C.C(N1CCC[C@H]1C(O)=O)(OCC1C=CC=CC=1)=O>CCO.[Pd]>[CH3:2][C@H:4]([NH:8][C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[C:5]([OH:7])=[O:6]

Participants

5

Reactant 2

HCID 83693Boc-L-ValineHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 85082Tert-butoxycarbonylalanine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Substantially the same procedure as described above was repeated except that N-t-BOC-L-valine (→P8) was used in place of the L-phenylalanine derivative. When N-CBZ-L-proline was used as starting material the deprotection was done by overnight hydrogenation with H2, 10% Pd/C in EtOH (→P9). In case of N-t-BOC-L-alanine the free amine was obtained after evaporation of the solvents and stirring the residue with saturated NaHCO3 solution (→P10).

Sources & evidence

ORD record
ord-d2561befc9224a639fd648a954bf6c19
Source dataset
uspto-grants-1997_09
Patent number
US05663174

Reaction notes

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