Sodium Hydroxide → (R)-1-(4'-(1-methyl-5-((1-phenylethoxy)carbonylamino)-1H-1,2,3-triazol-4-yl)biphenyl-3-yl)cyclopropanecarboxylic acid

HRID 631922Notes

Reaction equation

HRID 631922 reaction equation
C([O:3][C:4]([C:6]1([C:9]2[CH:10]=[C:11]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[N:22]=[N:23][N:24]([CH3:38])[C:25]=4[NH:26][C:27]([O:29][C@@H:30]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=4)[CH3:31])=[O:28])=[CH:17][CH:16]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+]>C1COCC1.C(O)C.O>[CH3:38][N:24]1[C:25]([NH:26][C:27]([O:29][C@@H:30]([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH3:31])=[O:28])=[C:21]([C:18]2[CH:19]=[CH:20][C:15]([C:11]3[CH:12]=[CH:13][CH:14]=[C:9]([C:6]4([C:4]([OH:5])=[O:3])[CH2:8][CH2:7]4)[CH:10]=3)=[CH:16][CH:17]=2)[N:22]=[N:23]1

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 118062400HCID 118062400, compound

Product 1

HCID 72704618(R)-1-(4'-(1-methyl-5-((1-phenylethoxy)carbonylamino)-1H-1,2,3-triazol-4-yl)biphenyl-3-yl)cyclopropanecarboxylic acidYield 88.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-1-(4′-(1-methyl-5-((1-phenylethoxy)carbonylamino)-1H-1,2,3-triazol-4-yl)biphenyl-3-yl)cyclopropanecarboxylic acid ethyl ester (90 mg, 0.176 mmol) in THF (5 mL) and ethanol (5 mL) was added an excess of sodium hydroxide (1.76 mL, 1.76 mmol, 1.0 M) in water at room temperature. The resulting colorless solution was stirred for 20 h at which time LCMS analysis indicated the absence of starting material. Then, the solvent was removed under vacuum and the basic aqueous layer was neutralized with 1.0 N HCl. The resulting white solids were collected by filtration and washed with water and hexanes. After air drying, 75 mg (88% yield) of the (R)-1-(4′-(1-methyl-5-((1-phenylethoxy)carbonylamino)-1H-1,2,3-triazol-4-yl)biphenyl-3-yl)cyclopropanecarboxylic acid was isolated as a white solid. LC/MS calcd. for C28H26N4O4 (m/e) 482.0, obsd. 483.1 (M+H, ES+).

Workup

  1. customThen, the solvent was removed under vacuum
  2. filtrationThe resulting white solids were collected by filtration
  3. washwashed with water and hexanes
  4. customAfter air drying

Sources & evidence

ORD record
ord-ca9541b86dd54df3bca02c30220b3470
Source dataset
uspto-grants-2016_04
Patent number
US09321738B2

Reaction notes

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