Acetic Acid → N-Acetyl-L-proline

HRID 1292328Notes

Reaction equation

HRID 1292328 reaction equation
[S-][C:2]#[N:3].[NH4+].[C:5]([OH:8])(=[O:7])[CH3:6].F[C:10](F)(F)[C:11]([OH:13])=O.[C:16](OC(=O)C)(=O)[CH3:17]>C(N(CC)CC)C>[C:11]([N:3]1[CH2:2][CH2:17][CH2:16][C@H:6]1[C:5]([OH:8])=[O:7])(=[O:13])[CH3:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 7918Acetic AnhydrideHCID 15666Ammonium thiocyanate

Product 1

HCID 66141N-Acetyl-L-proline

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

ammonium thiocyanate (BDH, Analar), Aristar acetic acid (BDH), eptide synthesis grades of trifluoroacetic acid and acetic anhydride (Applied Biosystems) were used without further purification. Reagents for amino acid analysis of phenylthiocarbamyl amino acids were all of the highest possible purity (Inglis et al Biochem. Biophys. Methods 15:249, 1988). Pierce 6M constant boiling HC1 and Analar phenol (BDH) were used for hydrolysis and N,N-diisopropylethylamine (DIEA, Peptide Synthesis Grade, Applied Biosystems) replaced triethylamine in the drying reagent and in the coupling buffer.

Workup

  1. customwere used without further purification
  2. customand Analar phenol (BDH) were used for hydrolysis and N,N-diisopropylethylamine (DIEA, Peptide Synthesis Grade, Applied Biosystems)

Sources & evidence

ORD record
ord-34e412f94b714d90839c31b45566e546
Source dataset
uspto-grants-1998_05
Patent number
US05756667

Reaction notes

Loading…