반응 #2020

반응 방정식

(R)-α-[N-(9-Fluorenylmethoxycarbonyl)amino]-benzenebutanoic acid

4-[N-methylamino]-2'-cyano-1,1'-biphenyl

oxalyl chloride

Triethylamine

→

(R)-α-[Amino]-N-methyl-N-[(2'-cyano)-[1,1'-biphenyl]-4-yl]benzenebutanamide

용매

methylene chloride

methylene chloride

반응 조건

후처리

1. 1
   기타was obtained
2. 2
   기타used without further purification
3. 3
   workup.STIRRINGthe reaction mixture stirred for a further 6 h
4. 4
   기타The reaction was quenched with 4-(aminomethyl)-piperidine (0.5 ml)
5. 5
   workup.STIRRINGstirred for 15 minutes
6. 6
   기타partitioned between water and methylene chloride
7. 7
   기타The organic phase was separated
8. 8
   기타dried
9. 9
   기타The volatiles were removed under reduced pressure
10. 10
    기타the residues chromatographed on silica gel

실험 절차

(R)-α-[N-(9-Fluorenylmethoxycarbonyl)amino]-benzenebutanoic acid (500 mg; 1.25 mmol), was converted into its corresponding acid chloride according to the procedure descibed in Example 33, Step F using 1 drop of DMF, oxalyl chloride (136 μl) in methylene chloride (2.5 ml). A yellow solid which was the acid chloride (525 mg) was obtained and used without further purification. A portion of the acid chloride (222.8 mg; 0.528 mmol) was added to 4-[N-methylamino]-2'-cyano-1,1'-biphenyl (110 mg; 0.528 mmol) were dissolved in methylene chloride (1 ml) and stirred together for 2 h at room temperature. Triethylamine (73.6 μl; 0.528 mmol) was added and the reaction mixture stirred for a further 6 h. The reaction was quenched with 4-(aminomethyl)-piperidine (0.5 ml) and stirred for 15 minutes and then partitioned between water and methylene chloride. The organic phase was separated, dried over powdered potassium carbonate. The volatiles were removed under reduced pressure and the residues chromatographed on silica gel using ethyl acetate and then ethyl acetate and methanol 9:1 v/v. The yield of the desired product was 60.2 mg (30.8%). FAB-MS:- calculated for C24H23N30 369.2 found 370.0 (M+1).

출처