تفاعل #1681714

معادلة التفاعل

diisoproylethylamine

D-valine tert-butyl ester

4-(4-bromophenoxy)benzene sulfonyl chloride

→

N-[4-(4-bromophenoxy)benzenesulfonyl]-D-valine t-butyl ester

المردود 64.0%

المذيبات

dichloromethane

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىThe ice bath was removed
2. 2
   workup.ADDITIONdiluted with 30 mL dichloromethane, and 30 ml of 1 M HCl
3. 3
   workup.ADDITIONwas added
4. 4
   أخرىThe layers were separated
5. 5
   غسيلthe aqueous layer was washed with 30 mL of dichloromethane
6. 6
   غسيلThe combined dichloromethane fractions were washed with brine
7. 7
   تجفيفdried over MgSO4
8. 8
   تركيزconcentrated
9. 9
   أخرىThe residue was chromatographed on silica
10. 10
    غسيلeluting with 25% ethyl acetate in hexane

الإجراء التجريبي

To a 0° C. suspension of 4-(4-bromophenoxy)benzene sulfonyl chloride (1.10 g, 3.16 mmol) in 20 mL of dichloromethane was added a solution of diisoproylethylamine (1.10 mL, 6.3 mmol) and D-valine tert-butyl ester (660 mg, 3.8 mol) in 11 mL of dichloromethane. The ice bath was removed, and the reaction was stirred for 3 h, diluted with 30 mL dichloromethane, and 30 ml of 1 M HCl was added. The layers were separated, and the aqueous layer was washed with 30 mL of dichloromethane. The combined dichloromethane fractions were washed with brine, dried over MgSO4, and concentrated. The residue was chromatographed on silica, eluting with 25% ethyl acetate in hexane, to give 980 mg (64%) of N-[4-(4-bromophenoxy)benzenesulfonyl]-D-valine t-butyl ester as a white foam.

المصدر