Reaction #4519

Reaction equation

palmitoyl-L-Ala-D-Glu(OH)OBzl

N-hydroxysuccinimide

dicyclohexylcarbodiimide

→

palmitoyl-L-Ala-D-Glu(OSu)OBzl

Solvents

tetrahydrofuran

chloroform

Conditions

Workup

1. 1
   Filtrationthe precipitate was filtered off
2. 2
   Washwashed with chloroform
3. 3
   ConcentrationThe filtrate was concentrated in vacuo
4. 4
   workup.ADDITIONthe diisopropylether was added to the residue
5. 5
   OtherThe product was collected
6. 6
   Otherdried

Procedure

To a solution of palmitoyl-L-Ala-D-Glu(OH)OBzl (1)(1.84 g) in a mixture of tetrahydrofuran (20 ml) and chloroform (30 ml) were added N-hydroxysuccinimide (425 mg) and dicyclohexylcarbodiimide (728 mg). The reaction mixture was kept for 18 hours at room temperature and the precipitate was filtered off and washed with chloroform. The filtrate was concentrated in vacuo and the diisopropylether was added to the residue. The product was collected and dried to afford palmitoyl-L-Ala-D-Glu(OSu)OBzl (2)(170 g).

Source