Water → HCID 54533981, 화합물

HRID 1482162노트

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HRID 1482162 반응식
[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]

참가 물질

8

반응물 4

HCID 962WaterHCID 6106L-LeucineHCID 516920Potassium bisulfateHCID 2724762tert-Butoxycarbonyl-L-isoleucine

생성물 1

HCID 54533981HCID 54533981, 화합물수율 89%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 5234Sodium Chloride용매2회HCID 7915Isopropyl Acetate용매

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온도
60 °C

실험 절차

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).

후처리

  1. customAfter evaporation of isopropyl acetate in vacuo
  2. distillationthe excess of water was eliminated by azeotropic distillation with isopropyl acetate
  3. customThe peptide precipitated during the concentration
  4. additionThe concentrated suspension was then diluted in cyclohexane
  5. filtrationfiltered
  6. customfinally dried in vacuum at 45° C

출처 및 근거

ORD 기록
ord-3cc998468f1244c1a303da34091dfb3f
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09409946B2

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