HCID 66655225, compound → HCID 86682580, compound

HRID 2036233Notes

Reaction equation

HRID 2036233 reaction equation
C(OC([N:11]1[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:20])[CH:17]=2)[CH:12]1[C:21]1[CH:26]=[C:25]([Cl:27])[CH:24]=[CH:23][C:22]=1[O:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])=O)C1C=CC=CC=1>CC(O)=O.Br>[ClH:27].[CH2:33]([O:32][C:30](=[O:31])[CH2:29][O:28][C:22]1[CH:23]=[CH:24][C:25]([Cl:27])=[CH:26][C:21]=1[CH:12]1[C:13]2[C:18](=[CH:17][C:16]([F:20])=[CH:15][CH:14]=2)[CH2:19][NH:11]1)[CH3:34]

Participants

4

Reactant 1

HCID 66655225HCID 66655225, compound

Product 1

HCID 86682580HCID 86682580, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 260Hydrogen BromideSolvent

Procedure

To a solution of (±)-1-(5-chloro-2-ethoxycarbonylmethoxy-phenyl)-5-fluoro-1,3-dihydro-isoindole-2-carboxylic acid benzyl ester (165 mg, 0.34 mmol, 1.0 eq.) in AcOH (3.0 mL), 33% hydrobromic acid in acetic acid (3.0 mL) was added. The mixture was stirred at r.t. for 2 hours. The reaction mixture was concentrated in vacuo. The residue was stirred in 1.25M HCl in ethanol (5.0 mL) at r.t. for 18 hours. The reaction mixture was concentrated in vacuo to give the desired salt as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. stirringThe residue was stirred in 1.25M HCl in ethanol (5.0 mL) at r.t. for 18 hours
  3. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-4b70829571c34d4f9d42a6966a84e13a
Source dataset
uspto-grants-2013_11
Patent number
US08575158B2

Reaction notes

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