Z-Sta-Ala-OC(CH3)3 → Z-Sta-Ala-OH

HRID 1982321Notes

Reaction equation

HRID 1982321 reaction equation
[NH:1]([C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C@H:2]([C@H:7]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([O:17]C(C)(C)C)=[O:16])[CH3:14])=[O:11])[OH:8])[CH2:3][CH:4]([CH3:6])[CH3:5]>FC(F)(F)C(O)=O>[NH:1]([C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23])[C@H:2]([C@H:7]([CH2:9][C:10]([NH:12][C@H:13]([C:15]([OH:17])=[O:16])[CH3:14])=[O:11])[OH:8])[CH2:3][CH:4]([CH3:6])[CH3:5]

Participants

3

Reactant 1

HCID 131714736Z-Sta-Ala-OC(CH3)3

Product 1

HCID 131714737Z-Sta-Ala-OH

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
25 °C

Procedure

470 mg of Z-Sta-Ala-OC(CH3)3 (from stage 13.1) are dissolved in 10 ml of trifluoroacetic acid and the solution is stirred for 10 minutes at 25° C. The solvent is then removed in a rotary evaporator and the residue is flash-chromatographed over 200 g of silica gel (eluant first chloroform/methanol/concentrated aqueous ammonia solution [40:10:1], then chloroform/methanol/concentrated aqueous ammonia solution [5:3:1]). The product-containing fractions are combined and concentrated by evaporation, the residue is taken up in chloroform and the chloroform solution is extracted with dilute hydrochloric acid and saturated sodium chloride solution, dried and concentrated by evaporation. After drying the residue in a high vacuum, Z-Sta-Ala-OH is obtained in the form of a colourless foam; Rf (G)=0.43.

Workup

  1. customThe solvent is then removed in a rotary evaporator
  2. customthe residue is flash-chromatographed over 200 g of silica gel (eluant first chloroform/methanol/concentrated aqueous ammonia solution [40:10:1]
  3. concentrationconcentrated by evaporation
  4. extractionthe chloroform solution is extracted with dilute hydrochloric acid and saturated sodium chloride solution
  5. customdried
  6. concentrationconcentrated by evaporation
  7. customAfter drying the residue in a high vacuum

Sources & evidence

ORD record
ord-e851fdd31e504198a633ac0f33e12bde
Source dataset
uspto-grants-1986_06
Patent number
US04595677

Reaction notes

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