Dicyclohexylcarbodiimide → HCID 19048628, compound

HRID 234090Notes

Reaction equation

HRID 234090 reaction equation
[C:1]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])(=[O:7])[CH2:2][CH2:3][C:4]([OH:6])=[O:5].O[N:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=[O:20].C1(N=C=NC2CCCCC2)CCCCC1.C(OCC)(=O)C.CCCCCC>O1CCCC1>[C:1]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])(=[O:7])[CH2:2][CH2:3][C:4]([O:6][N:14]1[C:18](=[O:19])[CH2:17][CH2:16][C:15]1=[O:20])=[O:5]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 41391074-(Tert-butoxy)-4-oxobutanoic acidHCID 21226206Ethyl acetate hexane

Product 1

HCID 19048628HCID 19048628, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Referring to Scheme 4, to a solution of 1.74 g (10 mmol) of tert-butyl hydrogen succinate (Buchi, G.; Roberts, C. J. Org Chem., 33:460, 1968) and 1.15 g (10 mmol) of N-hydroxy-succinimide in anhydrous tetrahydrofuran (20 ml) was added 2.06 g (10 mmol) of 1,3-dicyclohexylcarbodiimide. After stirring at room temperature overnight, the reaction was filtered to remove the dicyclohexylurea by-product. The filtrate was concentrated in vacuo to give a residue. Chromatography on silica gel using ethyl acetate-hexane (1:1), provided 2.3 g (84% yield) of tert-butyl succinimidyl succinate (4a) as a white solid. TLC: Rf 0.50 (ethyl acetate-hexane 1:1); NMR (d6 -DMSO) a 1.39(s, 9H), 2.56(m, 2H), 2.80(bs, 4H), 2.86 (m, 2H).

Workup

  1. filtrationthe reaction was filtered
  2. customto remove the dicyclohexylurea by-product
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give a residue

Sources & evidence

ORD record
ord-01d18f61cdbd4418b72616176c993222
Source dataset
uspto-grants-1997_01
Patent number
US05594106

Reaction notes

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