Sodium Hydroxide → (4-{4-[1-methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-1H-[1,2,3]triazol-4-yl]-phenyl}-cyclohexyl)-acetic acid

HRID 631937Notes

Reaction equation

HRID 631937 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][CH:6]1[CH2:11][CH2:10][CH:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[N:20][N:21]([CH3:35])[C:22]=3[NH:23][C:24]([O:26][C@@H:27]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH3:28])=[O:25])=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)C.[OH-].[Na+]>C1COCC1.C(O)C>[CH3:35][N:21]1[C:22]([NH:23][C:24]([O:26][C@@H:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH3:28])=[O:25])=[C:18]([C:15]2[CH:14]=[CH:13][C:12]([CH:9]3[CH2:10][CH2:11][CH:6]([CH2:5][C:4]([OH:36])=[O:3])[CH2:7][CH2:8]3)=[CH:17][CH:16]=2)[N:19]=[N:20]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 118061991(4-{4-[1-methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-1H-[1,2,3]triazol-4-yl]-phenyl}-cyclohexyl)-acetic acid ethyl ester

Product 1

HCID 71457482(4-{4-[1-methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-1H-[1,2,3]triazol-4-yl]-phenyl}-cyclohexyl)-acetic acidYield 71%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-{4-[1-methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-1H-[1,2,3]triazol-4-yl]-phenyl}-cyclohexyl)-acetic acid ethyl ester (15 mg, 0.031 mmol) in THF (2 mL) and ethanol (2 mL) was added a 1.0 M solution of sodium hydroxide (310 μL, 0.31 mmol) at room temperature. The resulting colorless solution was stirred for 15 h at which time TLC analysis indicated the absence of the starting material. Then, the solvent was removed under vacuum and the basic aqueous layer was neutralized with 1 N HCl. The resulting solids were collected by filtration and washed with water and hexanes. After air drying, (4-{4-[1-methyl-5-((R)-1-phenyl-ethoxycarbonylamino)-1H-[1,2,3]triazol-4-yl]-phenyl}-cyclohexyl)-acetic acid (10 mg, 71% yield) was isolated as a white solid. 1H NMR (DMSO-d6) δ ppm 12.04 (br. s., 1H), 9.85 (br. s., 1H), 7.62 (d, J=7.3 Hz, 2H), 6.84-7.54 (m, 7H), 5.78 (br. s., 1H), 3.83 (s, 3H), 2.16 (d, J=6.8 Hz, 2H), 1.65-1.93 (m, 5H), 1.39-1.64 (m, 5H), 1.01-1.35 (m, 3H). LC/MS calcd. for C26H30N4O4 (m/e) 462, obsd. 463.3 [M+H, ES+].

Workup

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

Sources & evidence

ORD record
ord-3c96a8eeb0be42f882a577f58d53b950
Source dataset
uspto-grants-2016_04
Patent number
US09321738B2

Reaction notes

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