1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → Boc-Phe-Phe-OEt

HRID 443730ノート

反応式

HRID 443730 の反応式
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:20][C@H:21]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.Cl.CCN=C=NCCCN(C)C>C(Cl)(Cl)Cl>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([NH:20][C@H:21]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 165085Ethyl L-phenylalaninate hydrochloride

生成物 1

HCID 12879039Boc-Phe-Phe-OEt収率 84.2%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

In 150 ml of chloroform were dissolved 26.5 g of Boc-Phe-OH and 22.9 g of H-Phe-OEt.HCl, to which 18.4 ml of WSC was added under cooling at 0° C. This was then subjected to stirring for 2 hours at -10° C., then 15 hours at room temperature. The reaction solution was concentrated in vacuo and the residue was dissolved in 20 ml of ethyl acetate, washed successively with 1 N HCl, water, 5% aqueous NaHCO3 solution and water, dried over Na2SO4 then again concentrated in vacuo. The thus obtained residue was added to n-hexane and the resultant amorphous precipitate was collected, and was recrystallized from n-hexane, which gave 37 g (yield=84%) of the title product. m.p. 106.5°-107.5° C. [α]D25 -9.7° (C 1.3, DMF). Analysis--Calculated for C25H32O5N2 : C, 68.16; H, 7.32; N, 6.36. Found: C, 67.85; H, 7.32; N, 6.49.

後処理

  1. custom15 hours
  2. customat room temperature
  3. concentrationThe reaction solution was concentrated in vacuo
  4. dissolutionthe residue was dissolved in 20 ml of ethyl acetate
  5. washwashed successively with 1 N HCl, water, 5% aqueous NaHCO3 solution and water
  6. dry with materialdried over Na2SO4
  7. concentrationthen again concentrated in vacuo
  8. additionThe thus obtained residue was added to n-hexane
  9. customthe resultant amorphous precipitate was collected
  10. customwas recrystallized from n-hexane, which

出典と根拠

ORDレコード
ord-24278a5661844520b7ffd5a29dea2c06
出典データセット
uspto-grants-1981_04
特許番号
US04261885

反応ノート

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