Dicyclohexylcarbodiimide → HCID 22594880, compound

HRID 1761294Notes

Reaction equation

HRID 1761294 reaction equation
[CH2:1]([N:8]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]([OH:17])=O)=[C:10]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]1=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:27][C:28]1[S:29][CH2:30][CH2:31][N:32]=1.CN(C1C=CC=CN=1)C.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH2:1]([N:8]1[C:13]([CH3:14])=[CH:12][C:11]([C:15]([N:32]2[CH2:31][CH2:30][S:29][C:28]2=[S:27])=[O:17])=[C:10]([O:18][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:9]1=[O:26])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 22594883HCID 22594883, compoundHCID 178527880HCID 178527880, compound

Product 1

HCID 22594880HCID 22594880, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-benzyl-3-benzyloxy-4-carboxy-6-methyl-2(1H)-pyridinone (5.36 g, 15.3 mmol) was dissolved in CH2Cl2 (100 ml) under an atmosphere of nitrogen. Then 2-mercaptothiazoline (1.88 g, 16.1 mmol) and dimethylaminopyridine (DMAP, 0.16 g, 1.0 mmol) were added and the solution stirred for 1 h. Dicyclohexylcarbodiimide (DCC, 3.45 g, 16.9 mmol) was then added in small portions and the reaction mixture stirred for 16 h, and then allowed to stand for 24 h at 0° C. The reaction mixture was filtered and the solvent removed by evaporation. EtOAc (10 ml) was added, and the solution filtered. This last step was repeated 3 times in order to remove the dicyclohexylurea (DCU), yielding a yellow oil. The product was purified by flash column chromatography (silica, CH2Cl2 as eluent). The solvents were removed by rotary evaporation, yielding a viscous yellow oil, which was recrystallized from acetone to give a yellow crystalline solid (Yield: 5.10 g, 74%). 1H NMR (CDCl3, 400 MHz): δ=7.12-7.49 (m, 10H, Bn), 5.98 (s, 1H, HOPO), 5.38 (s, 2H, Bn-CH2), 5.34 (s, 2H, Bn-CH2), 4.59 (t, J=7.3 Hz, 2H, thiaz), 2.90 (t, 2H, J=7.3 Hz, thiaz), 2.27 (s, 3H, HOPO CH3) ppm. Anal. Calcd (Found) for C24H22N2O3S2: C, 63.98 (64.04); H, 4.92 (5.02); N, 6.22 (6.03). FAB-MS (+): m/z: 451 [M+H]+.

Workup

  1. stirringthe reaction mixture stirred for 16 h
  2. waitto stand for 24 h at 0° C
  3. filtrationThe reaction mixture was filtered
  4. customthe solvent removed by evaporation
  5. additionEtOAc (10 ml) was added
  6. filtrationthe solution filtered
  7. customto remove the dicyclohexylurea (DCU)
  8. customyielding a yellow oil
  9. customThe product was purified by flash column chromatography (silica, CH2Cl2 as eluent)
  10. customThe solvents were removed by rotary evaporation
  11. customyielding a viscous yellow oil, which
  12. customwas recrystallized from acetone

Sources & evidence

ORD record
ord-e39a6c7949694041887a94becbd73d93
Source dataset
uspto-grants-2005_01
Patent number
US06846915B2

Reaction notes

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