Trifluoroacetic acid → HCID 86590469, compound

HRID 2308209Notes

Reaction equation

HRID 2308209 reaction equation
[CH2:1]([O:8][C:9](=[O:31])[C@H:10]([CH2:27][CH:28]([CH3:30])[CH3:29])[NH:11][C:12](=[O:26])[C@H:13]1[CH2:17][CH2:16][CH2:15][N:14]1C(=O)NOC(C)(C)C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl>[CH2:1]([O:8][C:9](=[O:31])[C@H:10]([CH2:27][CH:28]([CH3:29])[CH3:30])[NH:11][C:12](=[O:26])[C@H:13]1[CH2:17][CH2:16][CH2:15][NH:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86590470HCID 86590470, compound

Product 1

HCID 86590469HCID 86590469, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(t-Butoxycarbamoyl)-(D)-proline N-hydroxysuccinimide ester (10) (1.25 g, 4.0 mmol) and (L)-leucine benzyl ester (0.885 g, 4.0 mmol) were stirred at ambient temperature in acetonitrile (10 mL) for 14 h. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. The organic phase was separated and washed with 1N HCl, saturated NaHCO3, and saturated NaCl. After drying over anhydrous MgSO4, evaporation of solvent gave N-(t-butyoxycarbamoyl)-(D)-prolylleucine benzyl ester as a colorless oil. N-(t-Butoxycarbamoyl)-(D)-prolylleucine benzyl ester (1.38 g, 3.3 mmol) was stirred for one hour at ambient temperature with a 30% (v/v) solution of trifluroacetic acid in dichloromethane (20 mL). The solvent was removed by rotary evaporation and the residue partitioned between ethyl acetate and a 50% (v/v) solution of saturated aq. NaHCO3 and saturated aq. Na2CO3. The organic phase was separated, washed with saturated aq. NaCl, and dried over anhydrous MgSO4. Filtration and solvent evaporation gave (D)-prolylleucine benzyl ester as a white semi-solid.

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customthe residue partitioned between ethyl acetate
  3. customThe organic phase was separated
  4. washwashed with saturated aq. NaCl
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationFiltration and solvent evaporation

Sources & evidence

ORD record
ord-bc44aee0869d47309d5380cc10aa597a
Source dataset
uspto-grants-2004_12
Patent number
US06835727B2

Reaction notes

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