Tetrahydrofuran → HCID 178519734, compound

HRID 1041835Notes

Reaction equation

HRID 1041835 reaction equation
[CH2:1]([O:8][N:9]1[C:14](C(O)=O)=[CH:13][CH:12]=[CH:11][C:10]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH:19][C:20]1[S:21][CH2:22][CH2:23][N:24]=1.C1(N=C=NC2CCCCC2)CCCCC1.C1C[O:43][CH2:42]C1>>[CH2:1]([O:8][N:9]1[C:14]([SH:21]2[CH2:22][CH2:23][NH:24][C:20]2=[S:19])=[CH:13][CH2:12][C:11](=[C:42]=[O:43])[C:10]1=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 154505551-(Benzyloxy)-6-oxo-1,6-dihydropyridine-2-carboxylic acidHCID 178527880HCID 178527880, compound

Product 1

HCID 178519734HCID 178519734, compoundYield 83.7%

Procedure

To a solution of 1-benzyloxy-6-carboxy-2 (1H)-pyridinone (4.90 g, 20 mmol), 2-mercaptothiazoline (2.62 g, 22 mmol), and a catalytic amount of 4-dimethyl-aminopyridine (DMAP) in dry THF (50 mL), was added N,N′-dicyclohexylcarbodiimide (DCC) (4.6 g, 22 mmol). After stirring overnight, the dicyclohexylurea (DCU) solids are removed by filtration the yellow filtrate is removed by rotary evaporation to give a yellow solid. Crystallization from isopropanol-methylene chloride gives the title compound (5.80 g, 83.7%) as a pale yellow powder, m.p.: 135-7° C.

Workup

  1. customthe dicyclohexylurea (DCU) solids are removed by filtration the yellow filtrate
  2. customis removed by rotary evaporation
  3. customto give a yellow solid
  4. customCrystallization from isopropanol-methylene chloride

Sources & evidence

ORD record
ord-37b0709f14574092ad760bcf8171185e
Source dataset
uspto-grants-2013_10
Patent number
US08557601B2

Reaction notes

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