HCID 11175030, compound → HCID 14259928, compound

HRID 1589309Notes

Reaction equation

HRID 1589309 reaction equation
[CH2:1]([NH:9][C:10](=[O:24])[C@H:11]([CH2:20][CH:21]([CH3:23])[CH3:22])[NH:12]C(OC(C)(C)C)=O)[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>C(O)(C(F)(F)F)=O.C(Cl)Cl>[CH2:1]([NH:9][C:10](=[O:24])[C@H:11]([CH2:20][CH:21]([CH3:22])[CH3:23])[NH2:12])[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

3

Reactant 1

HCID 11175030HCID 11175030, compound

Product 1

HCID 14259928HCID 14259928, compound

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

N-(tertiarybutoxycarbonyl)-L-leucine N-phenethylamide (6.17 g, mole) was dissolved in a 1:1 TFA/CH2Cl2 mixture (60 ml). After stirring for 6 h at 20° the reaction mixture was concentrated in vacuo and the residue in CH2Cl2 (50 ml) washed with saturated aq. NaHCO3 (100 ml). The aqueous extract was back extracted with CH2Cl2 (50 ml×3) and the combined organic extracts concentrated to an oil in vacuo. The crude L-leucine N-phenethylamide so obtained was used as such in the next step.

Workup

  1. concentrationwas concentrated in vacuo
  2. washthe residue in CH2Cl2 (50 ml) washed with saturated aq. NaHCO3 (100 ml)
  3. extractionThe aqueous extract
  4. extractionwas back extracted with CH2Cl2 (50 ml×3)
  5. concentrationthe combined organic extracts concentrated to an oil in vacuo

Sources & evidence

ORD record
ord-91e27f83ae804d0c81156d6c5f9ccc88
Source dataset
uspto-grants-1986_02
Patent number
US04568666

Reaction notes

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