Dicyclohexylcarbodiimide → Acetic acid N-hydroxysuccinimide ester

HRID 2394237Notes

Reaction equation

HRID 2394237 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

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 3155947[(1-methyl-1h-tetrazol-5-yl)thio]acetic acid

Product 1

HCID 84460Acetic acid N-hydroxysuccinimide ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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.

Workup

  1. customAfter a few minutes white crystals were obtained
  2. filtrationThe crystals were filtered off
  3. customDimethylformamide was removed in vacuum
  4. customwas taken up in 60 ml ethyl acetate at 60° C.
  5. filtrationfiltered off
  6. washwashed with 30 ml ethylacetate (three times)
  7. customdried at high vacuum

Sources & evidence

ORD record
ord-1783160472344e6f93b5a7ecf9e68367
Source dataset
uspto-grants-1998_09
Patent number
US05811419

Reaction notes

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