Hydrochloric Acid → HCID 58024763, compound

HRID 1675675Notes

Reaction equation

HRID 1675675 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([NH:11][C:12]1[CH:24]=[CH:23][C:15]([C:16]([O:18]C(C)(C)C)=[O:17])=[CH:14][CH:13]=1)=[O:10].Cl.O1CCOCC1>ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([NH:11][C:12]1[CH:24]=[CH:23][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)=[O:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58024775HCID 58024775, compound2×

Product 1

HCID 58024763HCID 58024763, compoundYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1,1-dimethylethyl 4-[(8-bromooctanoyl)amino]benzoate (0.61 g, 1.5 mmol, as prepared in Intermediate 35) in dichloromethane (2 ml) was added a 4M solution of HCl in 1,4-dioxane (4 ml, about 10 equivalents), and the mixture was left to stand at ambient temperature for 18 hours. The mixture was evaporated to dryness and the residue was co-evaporated with dichloromethane (20 ml) to give the title compound as a white solid (0.51 g). LCMS showed MH+=342/344 (Br isotope pattern); TRET=3.34 min. NMR (d6-DMSO) suggested that the material was again about 75% pure and that the impurity from the previous reaction (Intermediate 35) was still present. The mixture was used without further purification.

Workup

  1. waitthe mixture was left
  2. customThe mixture was evaporated to dryness

Sources & evidence

ORD record
ord-4681d52437bd4c96a3ba6dd57ceabae3
Source dataset
uspto-grants-2011_08
Patent number
US08003663B2

Reaction notes

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