Boc-Leu-Ala-OBzl → H-Leu-Ala-OBzl

HRID 2081967Notes

Reaction equation

HRID 2081967 reaction equation
[NH:1]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:2]([C:7]([NH:9][C@H:10]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH3:11])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5]>FC(F)(F)C(O)=O>[NH:1]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:2]([C:7]([NH:9][C@H:10]([C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[CH3:11])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:12]([O:14][CH2:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[O:13])[CH3:11])=[O:8])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

4

Reactant 1

HCID 58901353Boc-Leu-Ala-OBzl

Product 2

HCID 16742166H-Leu-Ala-OBzlHCID 58901353Boc-Leu-Ala-OBzl

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Boc-Leu-Ala-OBzl was prepared by the procedure for dipeptide synthesis in Example 2. Boc-Leu-Ala-OBzl (23.7 g, 57.7 mmoles) was dissolved in 40 mL of anhydrous trifluoroacetic acid. After 15 min, excess trifluoroacetic acid was removed by evaporation and the residue was treated with ether to yield H-Leu-Ala-OBzl.trifluoroacetic acid as a crystalline product (22.8 g).

Workup

  1. customexcess trifluoroacetic acid was removed by evaporation
  2. additionthe residue was treated with ether

Sources & evidence

ORD record
ord-1f363856415640ab8c981b91f505f462
Source dataset
uspto-grants-1993_02
Patent number
US05187157

Reaction notes

Loading…