반응 #595320

반응 방정식

(S)-2-phenyl-2-tert-butoxycarbonylaminoethylazide

1-(trifluoroacetyl)indoline-5-sulfonyl chloride

Water

→

(S)-1-phenyl-1-(tert-butoxycarbonylamino)-2-(1-trifluoroacetylindoline-5-sulfonyl)aminoethane

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   기타The catalyst was separated by filtration
2. 2
   workup.ADDITIONTo the filtrate triethylamine (8 mL) was added
3. 3
   workup.STIRRINGthe mixture was shaken well
4. 4
   기타organic layer was separated
5. 5
   workup.STIRRINGshaken with 200 mL 2% citric acid
6. 6
   기타separated
7. 7
   건조dried with MgSO4
8. 8
   기타The drying agent was separated by filtration
9. 9
   농축The filtrate was concentrated
10. 10
    기타the title product was precipitated by addition of hexane

실험 절차

A mixture of (S)-2-phenyl-2-tert-butoxycarbonylaminoethylazide (10.50 g, 0.04 mol) dissolved in 250 mL dichloromethane and 2.5 g of 10% Pd/C was hydrogenated for 5 hrs at 70 psi of H2. The catalyst was separated by filtration. To the filtrate triethylamine (8 mL) was added, the mixture was cooled to −20° C. followed by slow addition of 1-(trifluoroacetyl)indoline-5-sulfonyl chloride (12.56 g, 0.04 mol) dissolved in 150 mL dichloromethane. The reaction mixture was then stirred overnight at room temperature. Water (500 mL) was added and the mixture was shaken well, organic layer was separated, shaken with 200 mL 2% citric acid, separated and dried with MgSO4. The drying agent was separated by filtration. The filtrate was concentrated and the title product was precipitated by addition of hexane. Yield: 17.67 g, (86%); (MH)+=514; 1H NMR (DMSO-d6): 1.33 (s, 9H), 2.85-2.99 (m, 2H), 3.26-3.30 (t, J=8.0 Hz, 2H), 4.31-4.35 (t, J=8.0 Hz, 2H), 4.53-4.59 (m, 1H), 7.19-7.35 (m, 6H), 7.66-7.68 (m, 2H), 7.72-7.75 (t, J=6.0 Hz, 1H), 8.13-8.15 (d, J=8.8 Hz, 1H).

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