Hydrochloric Acid → (2S)-2-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}-benzoylamino}-3-phenylpropionic acid

HRID 2305225Notes

Reaction equation

HRID 2305225 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:44]=[CH:45][CH:46]=4)[C:28]([NH:30][C@@H:31]([CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[C:32]([O:34]CC)=[O:33])=[O:29])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[Li+].O.Cl>O1CCCC1.CO.O>[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:44]=[CH:45][CH:46]=4)[C:28]([NH:30][C@@H:31]([CH2:37][C:38]4[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=4)[C:32]([OH:34])=[O:33])=[O:29])[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 57313302ethyl (2S)-2-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl)methyl}benzoylamino}-3-phenylpropionate

Product 1

HCID 57146223(2S)-2-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}-benzoylamino}-3-phenylpropionic acidYield 100%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of ethyl (2S)-2-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoylamino}-3-phenylpropionate (119 mg, 0.195 mmol) in tetrahydrofuran (4 ml) was added a solution of lithium hydroxide-water (16.4 mg, 0.390 mmol) in MeOH-water (1:1) (2.8 ml) at 5° C. The reaction mixture was stirred at the same temperature for 1 hour, and then stirred at room temperature for 30 minutes. To the reaction mixture was added 1N hydrochloric acid (0.5 ml) at 5° C. and extracted with EtOAc. The organic layer was washed with water and brine. The resultant mixture was dried over magnesium sulfate, and evaporated in vacuo to give (2S)-2-{3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}-benzoylamino}-3-phenylpropionic acid (113.0 mg, 100%).

Workup

  1. stirringstirred at room temperature for 30 minutes
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with water and brine
  4. dry with materialThe resultant mixture was dried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-91d5a501f95747788bf5f9687fb7468e
Source dataset
uspto-grants-2002_08
Patent number
US06437146B1

Reaction notes

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