Hydrochloric Acid → (S)-2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl)propionic acid

HRID 271844Notes

Reaction equation

HRID 271844 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C@@H:16]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([N:35]([CH3:46])[C:36]([NH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[O:37])[CH:30]=2)=[CH:25][CH:24]=1)[C:17]([O:19]CC)=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].Cl>O1CCCC1.CO.O>[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C@@H:16]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[C:31]([N:35]([CH3:46])[C:36]([NH:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[O:37])[CH:30]=2)=[CH:25][CH:24]=1)[C:17]([OH:19])=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 10371672ethyl (S)-2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propionate

Product 1

HCID 10483579(S)-2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl)propionic acidYield 77.5%

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

0.75 g (1.2 mmol) of ethyl (S)-2-(2-benzoylphenylamino)-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propionate (Example 1H) is dissolved in a mixture of 10 ml of tetrahydrofuran, 1 ml of methanol and a few drops of water. 86 mg (2 mmol) of lithium hydroxide are added. The medium is stirred for 6 h and then treated with an aqueous 1N hydrochloric acid solution, extracted with ethyl acetate, dried over magnesium sulfate, and concentrated. The residue obtained is purified by chromatography on a column of silica and eluted with a 1/1 heptane/ethyl acetate mixture. 0.55 g of (S)-2-(2-benzoylphenylamino)-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl)propionic acid is obtained with a 77% yield.

Workup

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

Sources & evidence

ORD record
ord-a5b26a357d9c427895a50c4deb0bbe10
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

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