Dicyclohexylcarbodiimide → HCID 12089328, compound

HRID 1761293Notes

Reaction equation

HRID 1761293 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:19])[NH:11][C:12]([CH3:18])=[CH:13][C:14]=1[C:15]([OH:17])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:20][C:21]1[S:22][CH2:23][CH2:24][N:25]=1.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1.CN(C1C=CN=CC=1)C>[CH2:1]([O:8][C:9]1[C:10](=[O:19])[NH:11][C:12]([CH3:18])=[CH:13][C:14]=1[C:15]([N:25]1[CH2:24][CH2:23][S:22][C:21]1=[S:20])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 22594876HCID 22594876, compoundHCID 178527880HCID 178527880, compound

Product 1

HCID 12089328HCID 12089328, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

3-benzyloxy-4-carboxy-6-methyl-2(1H)-pyridinone (5.39 g, 21.1 mmol) was dissolved in dry THF (200 ml). Then 2-mercaptothiazoline (2.71 g, 23.2 mmol) and DMAP (0.25 g, 2.0 mmol) were added and the solution stirred under an atmosphere of N2 for 1 h. Then dicyclohexylcarbodiimide (DCC, 5.12 g, 25.3 mmol) was added in small portions at intervals split over 3 hrs. The reaction was left to stir for 16h, and then left to stand at 0° C. for a further 24 h. The dicyclohexylurea (DCU) was removed by filtration, and the solvents removed. The remaining residue was dissolved in CH2Cl2, filtered and purified by a gradient flash silica column (2-6% CH3OH in CH2Cl2). The solvents were removed from the appropriate fractions by rotary evaporation, and the residue recrystallized from acetone, yielding yellow crystals (3.78 g, 56%). 1H NMR (CDCl3, 300 MHz): δ=7.32-7.47 (m, 5H, aromatic Bn), 5.98 (s, 1H, CH), 5.34 (s, 2H, Bn CH2), 4.34 (t, J=7.3 Hz, 2H, CH2) 2.92 (t, J=7.3 Hz, 2H, CH2), 2.34 (s, 3H, CH3) ppm. Anal. Calcd (Found) for C17H16N2O3S2: C, 56.65 (56.50); H, 4.47 (4.51); N, 7.77 (7.70). FAB-MS (+): m/z: 361[M+H]+.

Workup

  1. customsplit over 3 hrs
  2. waitThe reaction was left
  3. stirringto stir for 16h
  4. waitleft
  5. waitto stand at 0° C. for a further 24 h
  6. customThe dicyclohexylurea (DCU) was removed by filtration
  7. customthe solvents removed
  8. dissolutionThe remaining residue was dissolved in CH2Cl2
  9. filtrationfiltered
  10. custompurified by a gradient flash silica column (2-6% CH3OH in CH2Cl2)
  11. customThe solvents were removed from the appropriate fractions by rotary evaporation
  12. customthe residue recrystallized from acetone

Sources & evidence

ORD record
ord-af871ed0e702479c92c3e7a7e912ef82
Source dataset
uspto-grants-2005_01
Patent number
US06846915B2

Reaction notes

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