反応 #2501405

反応方程式

p-toluenesulfonic acid

5-aminopentanoic acid benzyl ester

HOSu

DCC

Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl

→

Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOH

溶媒

triethylamine

DMF

methanol

water

DMF

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred for 3 days at room temperature
2. 2
   濃縮The reaction mixture was concentrated
3. 3
   その他the residue was purified by column chromatography (CH2Cl2:MeOH=20:1)
4. 4
   その他to obtain 380 mg of Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl (Bzl represents benzyl group) (SEQ ID NO
5. 5
   workup.STIRRINGstirred overnight under hydrogen at ordinary pressure
6. 6
   その他The catalyst in the reaction mixture was removed by filtration
7. 7
   濃縮the filtrate was concentrated to dryness

実験手順

Boc-y-Gly-Gly-Phe-OH (575 mg) (SEQ ID NO. 8), HOSu (182 mg), and DCC (326 mg) were dissolved in DMF (20 ml), and the mixture was stirred for 30 minutes. The solution was added with a solution of p-toluenesulfonic acid salt of 5-aminopentanoic acid benzyl ester (500 mg) and triethylamine (0.184 ml) dissolved in DMF (10 ml), and the mixture was stirred for 3 days at room temperature. The reaction mixture was concentrated, and the residue was purified by column chromatography (CH2Cl2:MeOH=20:1) to obtain 380 mg of Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl (Bzl represents benzyl group) (SEQ ID NO. 8). The Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOBzl (SEQ ID NO. 8) (380 mg) was dissolved in methanol containing 50% of water (20 ml), and the solution was added with 5% Pd—C (water content; 50%, 300 mg) and stirred overnight under hydrogen at ordinary pressure. The catalyst in the reaction mixture was removed by filtration, and the filtrate was concentrated to dryness to obtain Boc-Gly-Gly-Gly-Phe-NH—(CH2)4—COOH (SEQ ID NO. 8) (330 mg).

出典