Water → HCID 54533981, compound
Reaction equation
[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([OH:9])=O)[C@H:3]([CH2:5][CH3:6])[CH3:4].[NH2:17][C@H:18]([C:23]([OH:25])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21].OS([O-])(=O)=O.[K+].O>CS(C)=O.C(OC(C)C)(=O)C.[Na+].[Cl-]>[NH:1]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C@H:2]([C:7]([NH:17][C@H:18]([C:23]([OH:25])=[O:24])[CH2:19][CH:20]([CH3:22])[CH3:21])=[O:9])[C@H:3]([CH2:5][CH3:6])[CH3:4]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 60 °C
Procedure
1.00 equivalent of Boc-Ile-NCA (Mw=257.3) was added to 1.10 equivalents of H-Leu-OH (Mw=131.2) in suspension in DMSO. The suspension was then heated at 60±5° C. at least 2 hours. After checking the conversion rate by HPLC, the reaction mixture was diluted with isopropyl acetate, washed by KHSO4 (Mw=136; 1.00 equivalent) in NaCl 5% (weight) aqueous, NaCl 5% (weight) aqueous and water. After evaporation of isopropyl acetate in vacuo, the excess of water was eliminated by azeotropic distillation with isopropyl acetate. The peptide precipitated during the concentration. The concentrated suspension was then diluted in cyclohexane. The precipitate was stirred at room temperature for at least 10 min, filtered and finally dried in vacuum at 45° C. The dried precipitate yielded 89% of Boc-Ile-Leu-OH as a white solid (based on NMR content).
Workup
- customAfter evaporation of isopropyl acetate in vacuo
- distillationthe excess of water was eliminated by azeotropic distillation with isopropyl acetate
- customThe peptide precipitated during the concentration
- additionThe concentrated suspension was then diluted in cyclohexane
- filtrationfiltered
- customfinally dried in vacuum at 45° C
Sources & evidence
- ORD record
- ord-3cc998468f1244c1a303da34091dfb3f
- Source dataset
- uspto-grants-2016_08
- Patent number
- US09409946B2
Reaction notes
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