Hydrochloric Acid → HCID 68415993, compound

HRID 1157490Notes

Reaction equation

HRID 1157490 reaction equation
[OH-].[Li+].[C:3]([CH2:11][NH:12][CH2:13][C:14]1[CH:15]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C@H:27]([NH:32][C:33]([CH3:43])=[CH:34][C:35](=[O:42])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:28]([O:30]C)=[O:29])=[CH:22][CH:21]=2)[CH:17]=[CH:18][CH:19]=1)(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl>CO.C1COCC1>[C:3]([CH2:11][NH:12][CH2:13][C:14]1[CH:15]=[C:16]([C:20]2[CH:25]=[CH:24][C:23]([CH2:26][C@H:27]([NH:32][C:33]([CH3:43])=[CH:34][C:35](=[O:42])[C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[C:28]([OH:30])=[O:29])=[CH:22][CH:21]=2)[CH:17]=[CH:18][CH:19]=1)(=[O:10])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 68418820HCID 68418820, compound

Product 1

HCID 68415993HCID 68415993, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

1.7 ml (1.70 mmol) of an aqueous 1M lithium hydroxide solution are added to a solution containing 620 mg (1.13 mmol) of methyl (S)-3-{3′-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-(1-methyl-3-oxo-3-phenylpropenylamino)propionate in 10 ml of a methanol/THF mixture (3/1). After stirring for 16 h, the medium is acidified with 1N hydrochloric acid until pH=4, extracted with ethyl acetate, dried over magnesium sulfate, and concentrated. The residue is purified by chromatography on a column of silica and eluted with a heptane/ethyl acetate mixture. 100 mg of (S)-3-{3′-[(benzoylmethylamino)methyl]biphenyl-4-yl}-2-(1-methyl-3-oxo-3-phenylpropenylamino)propionic acid are isolated with a 17% yield.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue is purified by chromatography on a column of silica
  5. washeluted with a heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-1e61edf55f8842319940dedb34095753
Source dataset
uspto-grants-2010_10
Patent number
US07807669B2

Reaction notes

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