Hydrochloric Acid → (3-{2-[(Benzyl-methoxycarbonyl-amino)-methyl]-4-bromo-phenoxy}-phenyl)-acetic acid

HRID 1969023Notes

Reaction equation

HRID 1969023 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([Br:18])=[CH:14][C:13]=2[CH2:19][N:20]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:21]([O:23][CH3:24])=[O:22])[CH:6]=1.[OH-].[Li+].Cl>C1COCC1>[CH2:25]([N:20]([CH2:19][C:13]1[CH:14]=[C:15]([Br:18])[CH:16]=[CH:17][C:12]=1[O:11][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:32])=[O:2])[CH:10]=[CH:9][CH:8]=1)[C:21]([O:23][CH3:24])=[O:22])[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58288472(3-{2-[(Benzyl-methoxycarbonyl-amino)-methyl]-4-bromo-phenoxy}-phenyl)-acetic acid methyl ester

Product 1

HCID 44538950(3-{2-[(Benzyl-methoxycarbonyl-amino)-methyl]-4-bromo-phenoxy}-phenyl)-acetic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To (3-{2-[(benzyl-methoxycarbonyl-amino)-methyl]-4-bromo-phenoxy}-phenyl)-acetic acid methyl ester (0.07 g) in THF (2 mL) was added 1N aqueous lithium hydroxide (2 mL), and the reaction was stirred at room temperature until no starting material was seen by analytical LCMS. The mixture was acidified with 1N aqueous HCl to pH 3-4, and extracted three times with EtOAc. The combined organic layers were washed with H2O, dried, and concentrated to give the title compound. M+H=485.

Workup

  1. extractionextracted three times with EtOAc
  2. washThe combined organic layers were washed with H2O
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-903d61c5c24a44259c853e77a3bddb62
Source dataset
uspto-grants-2013_04
Patent number
US08426449B2

Reaction notes

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