Hydrochloric Acid → 3-{3'-[(Tert-butoxycarbonylmethylamino)methyl]biphenyl-4-yl}-2-ethoxypropionic acid

HRID 730407Notes

Reaction equation

HRID 730407 reaction equation
[C:1]([O:5][C:6]([CH2:8][NH:9][CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH:24]([O:29][CH2:30][CH3:31])[C:25]([O:27]C)=[O:26])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[OH-].[Li+].Cl>O1CCCC1.C(OCC)(=O)C>[C:1]([O:5][C:6]([CH2:8][NH:9][CH2:10][C:11]1[CH:12]=[C:13]([C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH:24]([O:29][CH2:30][CH3:31])[C:25]([OH:27])=[O:26])=[CH:19][CH:18]=2)[CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 68850052Methyl 3-{3'-[(tert-butoxycarbonylmethylamino)methyl]biphenyl-4-yl}-2-ethoxypropionate

Product 1

HCID 688520833-{3'-[(Tert-butoxycarbonylmethylamino)methyl]biphenyl-4-yl}-2-ethoxypropionic acidYield 100.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

0.65 g (1.3 mmol) of methyl 3-{3′-[(tert-butoxycarbonylmethylamino)-methyl]biphenyl-4-yl}-2-ethoxypropionate is placed in 10 ml of tetrahydrofuran, 0.5 ml of methanol and 1.9 ml (1.9 mmol) of aqueous 1M lithium hydroxide solution. After stirring at room temperature for 2 hours, the reaction medium is diluted with ethyl acetate, acidified to pH 6 with aqueous 1N hydrochloric acid solution, extracted with ethyl acetate, dried over magnesium sulfate, filtered and concentrated. 0.54 g of 3-{3′-[(tert-butoxycarbonylmethylamino)methyl]biphenyl-4-yl}-2-ethoxypropionic acid is obtained in a yield of 92%.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5fec42d549c44d49abdc3ddecff830c8
Source dataset
uspto-grants-2009_09
Patent number
US07582663B2

Reaction notes

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