Water → HCID 23560767, compound

HRID 1058381Notes

Reaction equation

HRID 1058381 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:5]([OH:7])=[O:6].O[N:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=[O:22].Cl.CN(C)CCCN=C=NCC.O>O1CCCC1>[CH3:14][O:13][C:11](=[O:12])[C:10]1[CH:9]=[CH:8][C:4]([C:5]([O:7][N:16]2[C:20](=[O:21])[CH2:19][CH2:18][C:17]2=[O:22])=[O:6])=[CH:3][C:2]=1[Br:1]

Participants

6

Reactant 4

HCID 962WaterHCID 80170N-HydroxysuccinimideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 186730263-Bromo-4-(methoxycarbonyl)benzoic acid

Product 1

HCID 23560767HCID 23560767, compoundYield 99.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3-bromo-4-(methoxycarbonyl)benzoic acid (Example 76; 1.60 g, 6.2 mmol) in tetrahydrofuran (30 mL) was cooled to 10° C. and N-hydroxysuccinimide (781 mg, 6.8 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (1.20 g, 6.5 mmol) were added. The solution was allowed to stir at room temperature overnight, then water was added and the solution was concentrated in vacuo to remove tetrahydrofuran. The mixture was extracted with ethyl acetate and the extracts were dried (MgSO4), filtered and evaporated under reduced pressure to furnish 2-bromo-4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]benzoic acid methyl ester (2.20 g, quantitative yield).

Workup

  1. concentrationthe solution was concentrated in vacuo
  2. customto remove tetrahydrofuran
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialthe extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ae7ac29ac25d47e9807e90b17f63202a
Source dataset
uspto-grants-2003_02
Patent number
US06515124B2

Reaction notes

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