Hydrochloric Acid → {3-(s)-Benzyloxycarbamoyl-4-(s)-[4-(2-methyl-quinolin-4-ylmethoxy)-phenylcarbamoyl]-cyclohexyl}-acetic acid

HRID 61436Notes

Reaction equation

HRID 61436 reaction equation
C[O:2][C:3](=[O:44])[CH2:4][CH:5]1[CH2:10][CH2:9][C@H:8]([C:11](=[O:32])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=[C:23]([CH3:31])[CH:22]=3)=[CH:15][CH:14]=2)[C@@H:7]([C:33](=[O:43])[NH:34][O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH2:6]1.O.[OH-].[Li+].Cl>C1COCC1>[CH2:36]([O:35][NH:34][C:33]([C@@H:7]1[C@@H:8]([C:11](=[O:32])[NH:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][C:21]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=[C:23]([CH3:31])[CH:22]=3)=[CH:15][CH:14]=2)[CH2:9][CH2:10][CH:5]([CH2:4][C:3]([OH:44])=[O:2])[CH2:6]1)=[O:43])[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 87349143HCID 87349143, compound

Product 1

HCID 87348872{3-(s)-Benzyloxycarbamoyl-4-(s)-[4-(2-methyl-quinolin-4-ylmethoxy)-phenylcarbamoyl]-cyclohexyl}-acetic acidYield 90.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {3-(S)-benzyloxy carbamoyl-4-(S)-[4-(2-methyl-quinolin-4-ylmethoxy)-phenylcarbamoyl]-cyclohexyl}-acetic acid methyl ester (238 mg, 0.40 mmol) in THF (5 mL) was added water (3 mL) and lithium hydroxide (40 mg, 0.95 mmol). After stirring at ambient temperature for 4 h, the reaction mixture was acidified with 1 N HCl to a pH of ca. 5. The product was extracted with ethyl acetate (4×5 mL) and the combined organic layers were washed with brine (5 mL), dried (NaSO4), and the volatiles were removed in-vacuo to afford 210 mg (90%) of the desired carboxylic acid as a sticky oil that was used without further purification in the following coupling reaction. MS (ESI): 582 (M+H+).

Workup

  1. extractionThe product was extracted with ethyl acetate (4×5 mL)
  2. washthe combined organic layers were washed with brine (5 mL)
  3. dry with materialdried (NaSO4)
  4. customthe volatiles were removed in-vacuo

Sources & evidence

ORD record
ord-bdd44a812e344fbc860e31369f993ea0
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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