N-Hydroxysuccinimide → 2,3-Dihydroxy-5-(4-methyl-benzoyl)-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester

HRID 2251620Notes

Reaction equation

HRID 2251620 reaction equation
[OH:1][C:2]1[C:10]([OH:11])=[CH:9][C:8]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].O[N:22]1[C:26](=[O:27])[CH2:25][CH2:24][C:23]1=[O:28].C1(N=C=N)CCCCC1>C1COCC1>[O:28]=[C:23]1[CH2:24][CH2:25][C:26](=[O:27])[N:22]1[O:5][C:4](=[O:6])[C:3]1[CH:7]=[C:8]([C:12](=[O:20])[C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:9]=[C:10]([OH:11])[C:2]=1[OH:1]

Participants

5

Reactant 3

HCID 80170N-HydroxysuccinimideHCID 12048208N-CyclohexylcarbodiimideHCID 596430452,3-Dihydroxy-5-(4-methyl-benzoyl)-benzoic acid

Product 1

HCID 596430042,3-Dihydroxy-5-(4-methyl-benzoyl)-benzoic acid 2,5-dioxo-pyrrolidin-1-yl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,3-dihydroxy-5-(4-methyl-benzoyl)-benzoic acid (214 mg, 0.79 mmol) in 10 mL dry THF cooled to 0° C., N-hydroxysuccinimide (136 mg, 1.18 mmol, 1.5 eq.) and N-cyclohexylcarbodiimide, N′-methyl polystyrene HL (Novabiochem) (1.9 eq./g, 832 mg, 2 eq.) were added and the solution was stirred 14 h while the cooling bath slowly warmed up to r.t. The solution was filtered and the filtrate was evaporated under reduced pressure. The crude product was recrystallised from H2O to yield the desired product as a brownish solid.

Workup

  1. filtrationThe solution was filtered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe crude product was recrystallised from H2O

Sources & evidence

ORD record
ord-21c3dfd2e9dc4f5797e2b82d870b2288
Source dataset
uspto-grants-2008_01
Patent number
US07319101B2

Reaction notes

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