Z-Pro-Val-OtBu → Z-Pro-val-OH

HRID 1086116Notes

Reaction equation

HRID 1086116 reaction equation
[N:1]1([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][C@H:6]([C:10]([O:12]C(C)(C)C)=[O:11])[CH:7]([CH3:9])[CH3:8])=[O:4]>FC(F)(F)C(O)=O>[N:1]1([C:20]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:21])[CH2:19][CH2:18][CH2:17][C@H:2]1[C:3]([NH:5][C@H:6]([C:10]([OH:12])=[O:11])[CH:7]([CH3:8])[CH3:9])=[O:4]

Participants

3

Reactant 1

HCID 12286264Z-Pro-Val-OtBu

Product 1

HCID 73512Z-Pro-val-OH

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

2.63 g of Z-Pro-Val-OtBu are dissolved in 20 ml of 90% trifluoroacetic acid. The mixture is left to stand at room temperature for one hour, and is concentrated. The residue is triturated with water. The precipitate is filtered off with suction and dried over P2O5. For further purification, the product is chromatographed on silica gel in CH2Cl2 /CH30H/petroleum ether/acetic acid/water 18:1:2:0.1:0.1.

Workup

  1. waitThe mixture is left
  2. concentrationis concentrated
  3. customThe residue is triturated with water
  4. filtrationThe precipitate is filtered off with suction
  5. dry with materialdried over P2O5
  6. customFor further purification
  7. customthe product is chromatographed on silica gel in CH2Cl2 /CH30H/petroleum ether/acetic acid/water 18:1:2:0.1:0.1

Sources & evidence

ORD record
ord-52ffc8ad769b493bbb8bb86c7e324a86
Source dataset
uspto-grants-1991_04
Patent number
US05011825

Reaction notes

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