Acetic Acid → HCID 58179767, compound

HRID 2237458Notes

Reaction equation

HRID 2237458 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][O:17][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(O)=O.[Br:22]N1C(=O)CCC1=O.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([Br:22])[O:17][C:11]=2[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 19600211HCID 19600211, compound

Product 1

HCID 58179767HCID 58179767, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of the product from step h) (50 mg, 0.21 mmol) in CHCl3 (527 μl) and AcOH (527 μl) was treated with N-bromosuccinimide (38.1 mg, 0.21 mmol) at 22° C. After 1 hour, the contents were poured into sat. NaHCO3 and extracted with EtOAc (2×5 ml). The organic layer was washed with brine (1×5 ml), dried (MgSO4) and purified by preparative TLC (80% hexanes:20% EtOAc) providing 2-bromo-4,5,7,8-tetrahydro-furo[2,3-d]azepine-6-carboxylic acid tert-butyl ester which was directly treated with 4M HCl in dioxane (2 ml). The dioxane was evaporated and the residue was dissolved in MeOH and purified by preparative LC/MS providing 1.3 mg of the title compound. 1H NMR (CDCl3) 6.08 (s, 1H); 3.02-3.07 (m, 4H); 2.89-2.92 (m, 2H); 2.57-2.70 (m, 3H); MS: ESI (positive): 216, 218 (M+H).

Workup

  1. extractionextracted with EtOAc (2×5 ml)
  2. washThe organic layer was washed with brine (1×5 ml)
  3. dry with materialdried (MgSO4)
  4. custompurified by preparative TLC (80% hexanes:20% EtOAc)

Sources & evidence

ORD record
ord-775cb05e382742439a731d21ea6a3f88
Source dataset
uspto-grants-2010_05
Patent number
US07718647B2

Reaction notes

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