BOC-Val-MeLeu-Ala-Bzl → H-Val-MeLeu-Ala-Bzl

HRID 1583842Notes

Reaction equation

HRID 1583842 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:6]([N:8]([CH3:28])[C@H:9]([C:14]([NH:16][C@H:17]([C:19]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:20])[CH3:18])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])[CH:3]([CH3:5])[CH3:4]>FC(F)(F)C(O)=O>[NH2:1][C@H:2]([C:6]([N:8]([CH3:28])[C@H:9]([C:14]([NH:16][C@H:17]([C:19]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:20])[CH3:18])=[O:15])[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])[CH:3]([CH3:5])[CH3:4]

Participants

3

Reactant 1

HCID 131714436BOC-Val-MeLeu-Ala-Bzl

Product 1

HCID 131714437H-Val-MeLeu-Ala-Bzl

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

30.7 g (60.8 mMol) BOC-Val-MeLeu-Ala-Bzl dissolved in 100 ml trifluoroacetic acid are stirred for 2 hrs. at room temperature. The obtained solution is concentrated under vacuum and the residue diluted with 500 ml methylene chloride. The solution is washed 3× with 200 ml saturated potassium carbonate solution, ice being added, the aqueous phases extracted with 200 ml methylene chloride and the combined organic phases dried over potassium carbonate. The title compound is obtained as a pale-yellow oil after further filtration and concentration: rotation, [α]D25 =-87.1° (c=1.0 in chloroform).

Workup

  1. customat room temperature
  2. concentrationThe obtained solution is concentrated under vacuum
  3. additionthe residue diluted with 500 ml methylene chloride
  4. washThe solution is washed 3× with 200 ml saturated potassium carbonate solution, ice being
  5. additionadded
  6. extractionthe aqueous phases extracted with 200 ml methylene chloride
  7. dry with materialthe combined organic phases dried over potassium carbonate

Sources & evidence

ORD record
ord-33eae3069e5a427382b4dae5887c5b3f
Source dataset
uspto-grants-1985_11
Patent number
US04554351

Reaction notes

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