Water → HCID 54533981、化合物

HRID 1482161ノート

反応式

HRID 1482161 の反応式
[NH2:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].[NH:10]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:11]([C:16](ON1C(=O)CCC1=O)=[O:17])[C@H:12]([CH2:14][CH3:15])[CH3:13].OS([O-])(=O)=O.[K+].O>C(OC(C)C)(=O)C.[Na+].[Cl-]>[NH:10]([C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[C@H:11]([C:16]([NH:1][C@H:2]([C:7]([OH:9])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:17])[C@H:12]([CH2:14][CH3:15])[CH3:13]

参加物

7

反応物 4

HCID 962WaterHCID 6106L-Leucine2 回HCID 333451Boc-Ile-OSuHCID 516920Potassium bisulfate

生成物 1

HCID 54533981HCID 54533981、化合物収率 80%

試薬・触媒・溶媒 2

HCID 5234Sodium Chloride溶媒2 回HCID 7915Isopropyl Acetate溶媒

実験手順

1.01 equivalents of H-Leu-OH (Mw=131.2) was first silylated with 2.10 equivalents TMA (Mw=145.12) at about 50° C. until a clear solution was obtained. The solution was cooled to room temperature and diluted with isopropyl acetate. 1.00 equivalent of the Boc-Ile-OSu solid (Mw=328.26; 100.0%) was then added to silylated H-Leu-OH solution. The reaction mixture was further stirred at room temperature for at least 8 hours. After the completion of the reaction was confirmed by HPLC, the solution was quenched by adding DMAPA and water, washed with KHSO4 (1.00 equivalent) in 500 ml 5% (weight) aqueous NaCl solution; 500 ml 5% (weight) aqueous NaCl solution, and water. After evaporation of the 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 (based on NMR content) 80% of Boc-Ile-Leu-OH as white solid.

後処理

  1. customwas first silylated with 2.10 equivalents TMA (Mw=145.12) at about 50° C. until a clear solution
  2. customwas obtained
  3. customthe solution was quenched
  4. additionby adding DMAPA and water
  5. customAfter evaporation of the isopropyl acetate in vacuo
  6. distillationthe excess of water was eliminated by azeotropic distillation with isopropyl acetate
  7. customThe peptide precipitated during the concentration
  8. additionThe concentrated suspension was then diluted in cyclohexane
  9. stirringThe precipitate was stirred at room temperature for at least 10 min
  10. filtrationfiltered
  11. customfinally dried in vacuum at 45° C

出典と根拠

ORDレコード
ord-92b52ee179d84f77ac859962bb5b1206
出典データセット
uspto-grants-2016_08
特許番号
US09409946B2

反応ノート

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