Hydrochloric Acid → HCID 22105546, compound

HRID 1455943Notes

Reaction equation

HRID 1455943 reaction equation
[CH2:1]([O:8][C:9]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][C:10]=1[CH2:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH2:25][CH3:26])[C:20]([O:22]CC)=[O:21])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Na+].Cl>O.C1COCC1>[CH2:1]([O:8][C:9]1[CH:30]=[CH:29][C:28]([Br:31])=[CH:27][C:10]=1[CH2:11][NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH2:25][CH3:26])[C:20]([OH:22])=[O:21])=[CH:15][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 22105549HCID 22105549, compound

Product 1

HCID 22105546HCID 22105546, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-[4-(2-benzyloxy-5-bromobenzylamino)phenyl]butanoate (4.2 g) was diluted in a solution of methanol (20 ml) and THF (20 ml). A 2N aqueous solution of sodium hydroxide was added and the mixture stirred at ambient temperature for 18 hours. The volume of solvent was reduced to half the original volume and water (20 ml) added. The mixture was acidified with 2N HCl to pH 3 and extracted with ethyl acetate (3×50 ml). The combined extracts were dried (MgSO4) and evaporated and the residue was subjected to chromatography, eluting with 10% EtOAc/CH2Cl2, to give 2-[4-(2-benzyloxy-5-bromobenzylamino)phenyl]butanoic acid (yield 1.31 gum).

Workup

  1. additionadded
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. dry with materialThe combined extracts were dried (MgSO4)
  4. customevaporated
  5. washeluting with 10% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-8b8e8b4b7f954e48a89f537db832027a
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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