BOC-D-alanine → Boc-(D)Ala-Gly-OBzl

HRID 652375ノート

反応式

HRID 652375 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

HCID 15567200Boc-(D)Ala-Gly-OBzl収率 90.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-704b84efe0ee494a8263c3f78ceb2203
出典データセット
uspto-grants-1987_06
特許番号
US04670540

反応ノート

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