BOC-D-alanine → Boc-(D)Ala-Gly-OBzl

HRID 652375노트

반응식

HRID 652375 반응식
[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:2]([C:4]([OH:6])=O)[CH3:3].CC1C=CC(S(O)(=O)=O)=CC=1.[CH:25]1[CH:30]=[CH:29][C:28]([CH2:31][O:32][C:33]([CH2:35][NH2:36])=[O:34])=[CH:27][CH:26]=1>C(Cl)Cl>[NH:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:2]([C:4]([NH:36][CH2:35][C:33]([O:32][CH2:31][C:28]1[CH:29]=[CH:30][CH:25]=[CH:26][CH:27]=1)=[O:34])=[O:6])[CH3:3]

참가 물질

4

반응물 2

HCID 637606BOC-D-alanineHCID 6451311O-benzylglycine toluene-p-sulphonate

생성물 1

HCID 15567200Boc-(D)Ala-Gly-OBzl수율 90.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Boc-D-Ala-OH (5.68 g, 30 mmole) and H-Gly-OBzl.TosOH (10.6 g, 1.05 eq) were suspended in CH2Cl2. WSCI (6 ml, 1.1 eq) was added dropwise while cooling, and the solution was stirred overnight. The CH2Cl2 was distilled off. The residue was dissolved in AcOEt (500 ml); washed with 1N HCl, water, 5% NaHCO3, and water in order; and dried over Na2SO4. AcOEt was distilled off, and the residue was recrystalized twice with AcOEt/n-hexane to give the desired product (9.16 g, 90.7%).

후처리

  1. additionWSCI (6 ml, 1.1 eq) was added dropwise
  2. temperaturewhile cooling
  3. distillationThe CH2Cl2 was distilled off
  4. dissolutionThe residue was dissolved in AcOEt (500 ml)
  5. washwashed with 1N HCl, water, 5% NaHCO3, and water in order
  6. dry with materialand dried over Na2SO4
  7. distillationAcOEt was distilled off
  8. customthe residue was recrystalized twice with AcOEt/n-hexane

출처 및 근거

ORD 기록
ord-704b84efe0ee494a8263c3f78ceb2203
출처 데이터셋
uspto-grants-1987_06
특허 번호
US04670540

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