Dicyclohexylcarbodiimide → Acetic acid N-hydroxysuccinimide ester

Reaction equation

CN1C(S[CH2:8][C:9]([OH:11])=[O:10])=NN=N1.O[N:13]1[C:17](=[O:18])[CH2:16][CH2:15][C:14]1=[O:19].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[O:19]=[C:14]1[CH2:15][CH2:16][C:17](=[O:18])[N:13]1[O:11][C:9](=[O:10])[CH3:8]

Participants

Procedure

5.2 g (885 mmol) (1-methyl-1H-tetrazol-5-ylsulfanyl)-acetic acid (CAS Reg. No 55862-52-7; Saito, Seiki et al, Synlett (1993), 2, 139-40 ; 29) were dissolved in 100 ml dimetylformamide. Then 3.44 g (32.84 mmol) N-hydroxysuccinimide were added. Then 6.78 g N,N'-dicyclohexylcarbodiimid were added. After a few minutes white crystals were obtained. The suspension was stirred for further five days. The crystals were filtered off. Dimethylformamide was removed in vacuum. The residue was taken up in 60 ml ethyl acetate at 60° C., filtered off, washed with 30 ml ethylacetate (three times) and dried at high vacuum. 1-Methyl-1H-tetrazol-5-ylsulfanyl)-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester was obtained.