Lithium Hydroxide → 2-[(2,4-Dichloro-benzoyl)-prop-2-ynyl-amino]-3-phenyl-propionic acid

HRID 2179934Notes

Reaction equation

HRID 2179934 reaction equation
C[O:2][C:3](=[O:26])[CH:4]([N:12]([C:16](=[O:25])[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=1[Cl:24])[CH2:13][C:14]#[CH:15])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[OH-].[Li+]>C1COCC1.CO.O>[Cl:24][C:18]1[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:17]=1[C:16]([N:12]([CH2:13][C:14]#[CH:15])[CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[C:3]([OH:26])=[O:2])=[O:25]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 207793042-[(2,4-Dichloro-benzoyl)-prop-2-ynyl-amino]-3-phenyl-propionic acid methyl ester

Product 1

HCID 224901382-[(2,4-Dichloro-benzoyl)-prop-2-ynyl-amino]-3-phenyl-propionic acid

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a THF:MeOH:H2O (3:2:1) (3 mL) solution of 2-[(2,4-Dichloro-benzoyl)-prop-2-ynyl-amino]-3-phenyl-propionic acid methyl ester (30 mg, 0.076 mmol), 1N aqueous solution of lithium hydroxide (0.46 mL, 0.46 mmol) was added and the reaction mixture was stirred at room temperature for 6 h. Solvents were removed under reduced pressure and the residue was partitioned between ethyl acetate and water. The water layer was acidified using 10% KHSO4 solution and then the organic layer was separated, dried (Na2SO4), concentrated. The residue was purified by column chromatography (ethyl acetate:hexane 1:1 to ethyl acetate) to obtain 2-[(2,4-dichloro-benzoyl)-prop-2-ynyl-amino]-3-phenyl-propionic acid, 23 mg (81%) as a white solid. The compound contains two other minor rotamers. 1H NMR (CDCl3, 400 MHz): δ7.45-7.05 (m, 8H), 6.77 (dd, minor rotamer), 5.70 (d, minor rotamer), 4.99 (bs, minor rotamer), 4.64-4.59 (m, minor rotamer), 4.28 (d, minor rotamer), 4.29-4.18 (m, minor rotamer), 3.79-3.09 (m, 5H), 2.37 (t, minor rotamer), 2.31 (t, minor rotamer), 2.17 (t, 1H). ESI− (M−H): 375.

Workup

  1. customSolvents were removed under reduced pressure
  2. customthe residue was partitioned between ethyl acetate and water
  3. customthe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography (ethyl acetate:hexane 1:1 to ethyl acetate)

Sources & evidence

ORD record
ord-7579c4bc3f3d45f188b14f323c2e2235
Source dataset
uspto-grants-2005_05
Patent number
US06887877B2

Reaction notes

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