N-(3-pyridylacetyl)-(L)-valine-tert-butyl ester → N-(3-Pyridylacetyl)-(L)-valine

HRID 1291764Notes

Reaction equation

HRID 1291764 reaction equation
C([O:5][C:6](=[O:21])[C@H:7]([CH:18]([CH3:20])[CH3:19])[NH:8][C:9](=[O:17])[CH2:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)(C)(C)C>FC(F)(F)C(O)=O.C(Cl)Cl>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([CH2:10][C:9]([NH:8][C@H:7]([C:6]([OH:21])=[O:5])[CH:18]([CH3:20])[CH3:19])=[O:17])[CH:12]=1

Participants

3

Reactant 1

HCID 18659858N-(3-pyridylacetyl)-(L)-valine-tert-butyl ester

Product 1

HCID 54304135N-(3-Pyridylacetyl)-(L)-valine

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

3.4 g of N-(3-pyridylacetyl)-(L)-valine-tert-butyl ester are dissolved in 20 ml of trifluoroacetic acid/methylene chloride (1:1) and the solution is stirred at RT for 16 h. The reaction solution is fully concentrated by evaporation and the residue is digested with DIPE. The title compound is obtained in the form of a white amorphous solid. 1H-NMR (200 MHz, CD3OD): 8.9-8.6 (m, broad, 1H), 8.5 (m, 1H), 7.95 (m, 1H), 4.33 (m, 1H), 3.93 (s, 2H), 2.2 (m, 1H), 0.98 (2d, 6H).

Workup

  1. concentrationThe reaction solution is fully concentrated by evaporation

Sources & evidence

ORD record
ord-69e67bb914954d6e9e9fd3f6666fc517
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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