1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → BOC-Ala-Gly-OBzl

HRID 2083808

反応式

HRID 2083808 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.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>C1COCC1>[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

6

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 85082Tert-butoxycarbonylalanineHCID 6451311O-benzylglycine toluene-p-sulphonate

生成物 1

HCID 10980600BOC-Ala-Gly-OBzl収率 85.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

BOC-Ala-OH (94.6 g.), H-Gly-OBzl.TosOH (168.8 g.) and HOBT (67.6 g.) were dissolved in THF (450 ml.) and WSC (91.5 ml.) was added thereto, then stirred for 1 hour at 0° C. and overnight at room temperature. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (800 ml.). 1 N HCl (500 ml.) was added, the precipitate was removed by filtration, and the ethyl acetate layer was washed with 1 N HCl (400 ml.), and twice with 5% sodium bicarbonate solution and water in this order, and, after drying with anhydrous magnesium sulfate, concentrated in vacuo. The residue was treated with n-hexane to obtain crude material (152.5 g.) Recrystallization was carried out twice by ethyl acetate - n-hexane to obtain BOC-Ala-Gly-OBzl (144 g., Yield: 85.7%, m.p.: 87° - 88.5° C., TLC: one spot, RF1 = 0.59).

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate (800 ml.)
  3. addition1 N HCl (500 ml.) was added
  4. customthe precipitate was removed by filtration
  5. washthe ethyl acetate layer was washed with 1 N HCl (400 ml.)
  6. dry with materialtwice with 5% sodium bicarbonate solution and water in this order, and, after drying with anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. additionThe residue was treated with n-hexane
  9. customto obtain
  10. customcrude material (152.5 g.) Recrystallization

出典と根拠

ORDレコード
ord-4092fed051d944afb234471f8ff76fa9
出典データセット
uspto-grants-1978_04
特許番号
US04086221

関連ノート

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