Potassium Carbonate → (2S)-3-(4-carbamoylphenyl)-2-[[1-cyclohexyl-2-(3-furyl)benzimidazole-5-carbonyl]amino]propanoic acid

HRID 2117002Notes

Reaction equation

HRID 2117002 reaction equation
C([O:3][C:4](=[O:38])[C@@H:5]([NH:15][C:16]([C:18]1[CH:37]=[CH:36][C:21]2[N:22]([CH:30]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[C:23]([C:25]3[CH:29]=[CH:28][O:27][CH:26]=3)=[N:24][C:20]=2[CH:19]=1)=[O:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[CH:9][CH:8]=1)C.C(=O)([O-])[O-:40].[K+].[K+]>CC(C)=O.O>[C:13]([C:10]1[CH:11]=[CH:12][C:7]([CH2:6][C@H:5]([NH:15][C:16]([C:18]2[CH:37]=[CH:36][C:21]3[N:22]([CH:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)[C:23]([C:25]4[CH:29]=[CH:28][O:27][CH:26]=4)=[N:24][C:20]=3[CH:19]=2)=[O:17])[C:4]([OH:3])=[O:38])=[CH:8][CH:9]=1)(=[O:40])[NH2:14]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 59909984(S)-3-(4-Cyanophenyl)-2-{(1-(1-cyclohexyl-2-furan-3-yl-1H-benzoimidazol-5-yl)-methanoyl]-amino}-propionic acid ethyl ester

Product 1

HCID 491242(2S)-3-(4-carbamoylphenyl)-2-[[1-cyclohexyl-2-(3-furyl)benzimidazole-5-carbonyl]amino]propanoic acid

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

(S)-3-(4-Cyanophenyl)-2-{[1-(1-cyclohexyl-2-furan-3-yl-1H-benzoimidazol-5-yl)-methanoyl]-amino}-propionic acid ethyl ester from example 10 (0.120 g, 0.235 mmol) was dissolved in a mixture of acetone (5 mL) and water (3 mL). Urea-hydrogen peroxide complex (1.0 mmol, 0.094 g) and potassium carbonate (10 mg) were added and the mixture stirred until completion (HPLC). The reaction mixture was concentrated under reduced pressure, the residue was dissolved in DMSO (1.5 mL) and 5 N NaOH (0.2 mL) was added. After stirring for 30 min at room temperature, TFA (0.5 mL) was added and the product isolated by prep HPLC (18 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in DMSO (1.5 mL)
  3. addition5 N NaOH (0.2 mL) was added
  4. stirringAfter stirring for 30 min at room temperature
  5. additionTFA (0.5 mL) was added
  6. customthe product isolated by prep HPLC (18 mg)

Sources & evidence

ORD record
ord-c0739d34d7fe4d67ad8a49745c91cf34
Source dataset
uspto-grants-2008_10
Patent number
US07439258B2

Reaction notes

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