HCID 11175030, compound → HCID 14259928, compound

HRID 1980835Notes

Reaction equation

HRID 1980835 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-c5df1e5baedd4221a8a1e3d9a73a5522
Source dataset
uspto-grants-1985_04
Patent number
US04511504

Reaction notes

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