BOC-MeLeu-Ala-Bzl → H-MeLeu-Ala-Bzl

HRID 1583840Notes

Reaction equation

HRID 1583840 reaction equation
[C:1]([N:8](C)[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])(OC(C)(C)C)=O>FC(F)(F)C(O)=O>[NH:8]([CH3:1])[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]

Participants

3

Reactant 1

HCID 131713049BOC-MeLeu-Ala-Bzl

Product 1

HCID 131714435H-MeLeu-Ala-Bzl

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

46.8 g (115 mMol) BOC-MeLeu-Ala-Bzl are dissolved in 100 ml trifluoroacetic acid pre-cooled to 0° C. and allowed to stand for 1 hr. at 0° C. and 1/2 hr. at room temperature. The obtained solution is concentrated under vacuum, diluted with 500 ml methylene chloride, poured onto ice and washed with 300 ml saturated potassium carbonate solution. The aqueous phase is extracted with 200 ml methylene chloride, the combined organic phases dried over potassium carbonate, filtered and concentrated. The residue is chromatographed on 2 kg silica gel 60 (0.063-0.24 mm) using 5% methanol in methylene chloride as eluant to yield the title compound: rotation, [α]D25 =-44.5° (c=1.0 in chloroform).

Workup

  1. customat 0° C.
  2. custom1/2 hr
  3. customat room temperature
  4. concentrationThe obtained solution is concentrated under vacuum
  5. additiondiluted with 500 ml methylene chloride
  6. additionpoured onto ice
  7. washwashed with 300 ml saturated potassium carbonate solution
  8. extractionThe aqueous phase is extracted with 200 ml methylene chloride
  9. dry with materialthe combined organic phases dried over potassium carbonate
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe residue is chromatographed on 2 kg silica gel 60 (0.063-0.24 mm)

Sources & evidence

ORD record
ord-a9d2566db9af452b99477a67b1d34fb9
Source dataset
uspto-grants-1985_11
Patent number
US04554351

Reaction notes

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