Diethyl Ether → Aconitic Acid

HRID 1648200

反応式

HRID 1648200 の反応式
[CH2:1]([C:10]([OH:12])=[O:11])/[C:2](/[C:7]([OH:9])=[O:8])=[CH:3]\[C:4]([OH:6])=[O:5].C1N=CN(C(N2C=NC=C2)=O)C=1.FC(F)(F)S(O)(=O)=O.C1(SC)C=CC=CC=1.C1C(O)=CC=CC=1C.CCOCC>CN(C=O)C.FC(F)(F)C(O)=O.O>[C:10]([OH:12])(=[O:11])[CH:1]=[C:2]([CH2:3][C:4]([OH:6])=[O:5])[C:7]([OH:9])=[O:8]

参加物

8

反応物 4

HCID 3283Diethyl EtherHCID 682631,1'-CarbonyldiimidazoleHCID 444212trans-Aconitic acidHCID 88261696Trifluoromethanesulfonic acid thioanisole m-cresol

生成物 1

HCID 309Aconitic Acid

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 6422Trifluoroacetic acid溶媒2 回

実験手順

Trans-aconitic acid (0.17 g, 1.0 mmol) and trifluoroacetic acid salt of β-Ala--Arg(Mts)--Leu--Asp(OBn)--Ser(Bn)--NH--iPr (SEQ ID NO:11) (3.23 g, 3.0 mmol) were condensed with CDI in DMF. The product was treated as in Example 73 to obtain the objective compound in the protected form (0.67 g, 0.22 mmol). The protected compound was dissolved in trifluoroacetic acid (10 ml), added with a trifuluoroacetic acid solution of 1M-trifluoromethanesulfonic acid/thioanisole/m-cresol with ice cooling at 0° C. and allowed to react for 1 hour to eliminate the protective group on the side chains and at the terminal of the peptide. The reaction mixture was poured into ether, and resulted oily precipitate was dissolved in distilled water, washed with ethyl acetate, passed through an anion-exchange resin column (Amberlite IRA400; C1 form) to convert the product into hydrochloride and lyophilized to obtain the objective aconitic acid (β-Ala--Arg--Leu--Asp--Ser--NH--iPr)3 (SEQ ID NO:11)3 (0.29 g, 0.15 mmol).

後処理

  1. additionThe product was treated as in Example 73
  2. customto obtain the objective compound in the protected form (0.67 g, 0.22 mmol)
  3. customto react for 1 hour
  4. customresulted oily precipitate
  5. washwashed with ethyl acetate

出典と根拠

ORDレコード
ord-4b5f55f6c5894670ac2dba04d8ff9f08
出典データセット
uspto-grants-1995_07
特許番号
US05436221

関連ノート

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