Dicyclohexylcarbodiimide → HCID 86747889, compound

HRID 1034373Notes

Reaction equation

HRID 1034373 reaction equation
[OH:1][C:2]1[C:11]2[C@H:10]3[CH2:12][C:13]([C:16]([OH:18])=[O:17])=[CH:14][CH2:15][C@@H:9]3[C:8]([CH3:20])([CH3:19])[O:7][C:6]=2[CH:5]=[C:4]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:3]=1.C1(N=C=NC2CCCCC2)CCCCC1.O[N:42]1[C:46](=[O:47])[CH2:45][CH2:44][C:43]1=[O:48]>C1COCC1>[OH:1][C:2]1[C:11]2[C@H:10]3[CH2:12][C:13]([C:16]([O:18][N:42]4[C:46](=[O:47])[CH2:45][CH2:44][C:43]4=[O:48])=[O:17])=[CH:14][CH2:15][C@@H:9]3[C:8]([CH3:19])([CH3:20])[O:7][C:6]=2[CH:5]=[C:4]([CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH:3]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 57264109HCID 57264109, compound

Product 1

HCID 86747889HCID 86747889, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

With reference to scheme 3, to a solution of (XVIII) (6 mg, 0.017 mmol) in dry THF (2 mL), under argon, was added dicyclohexylcarbodiimide (Aldrich; 13 mg, 0.063 mmol) and N-hydroxysuccinimide (Aldrich; 11 mg, 0.096 mmol). The resulting reaction mixture was stirred for 43 h, filtered from dicyclohexylurea, and the filtrate evaporated in vacuo to afford white solids. This material was digested with a small volume of THF and the insoluble part (urea) was filtered off. The filtrate was evaporated in vacuo to dryness and the process repeated to give a foam which was subjected to preparative TLC on silica, eluting with EtOAc-hexanes (1:1), to give 5 mg, 67%, of the NHS ester as an off-white foam.

Workup

  1. customThe resulting reaction mixture
  2. filtrationfiltered from dicyclohexylurea
  3. customthe filtrate evaporated in vacuo
  4. customto afford white solids
  5. filtrationthe insoluble part (urea) was filtered off
  6. customThe filtrate was evaporated in vacuo to dryness
  7. customto give a foam which
  8. washeluting with EtOAc-hexanes (1:1)
  9. customto give 5 mg, 67%

Sources & evidence

ORD record
ord-14e7055fe8f94a8796382090b7d595fa
Source dataset
uspto-grants-1994_05
Patent number
US05315015

Reaction notes

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