Reaction #595320

Reaction equation

(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

Solvents

dichloromethane

dichloromethane

Conditions

Workup

1. 1
   OtherThe 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
   Otherorganic layer was separated
5. 5
   workup.STIRRINGshaken with 200 mL 2% citric acid
6. 6
   Otherseparated
7. 7
   Dryingdried with MgSO4
8. 8
   OtherThe drying agent was separated by filtration
9. 9
   ConcentrationThe filtrate was concentrated
10. 10
    Otherthe title product was precipitated by addition of hexane

Procedure

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).

Source