Hydrochloric Acid → HCID 87348293, compound

HRID 61432Notes

Reaction equation

HRID 61432 reaction equation
C[O:2][C:3](=[O:36])[CH2:4][CH:5]1[CH2:10][CH2:9][C@H:8]([C:11]([N:13]2[CH2:18][CH2:17][N:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:15][CH2:14]2)=[O:12])[C@@H:7]([C:25](=[O:35])[NH:26][O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:6]1.O.[OH-].[Li+].Cl>C1COCC1>[CH2:28]([O:27][NH:26][C:25]([C@@H:7]1[C@@H:8]([C:11]([N:13]2[CH2:14][CH2:15][N:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:17][CH2:18]2)=[O:12])[CH2:9][CH2:10][CH:5]([CH2:4][C:3]([OH:36])=[O:2])[CH2:6]1)=[O:35])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 87348205HCID 87348205, compound

Product 1

HCID 87348293HCID 87348293, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [3-(S)-benyloxycarbamoyl-4-(S)-(4-phenyl-piperazine-1-carbonyl)-cyclohexyl]-acetic acid methyl ester (213 mg, 0.432 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 154 mg (87%) of [3-(S)-benyloxycarbamoyl-4-(S)-(4-phenyl-piperazine-1-carbonyl)-cyclohexyl]-acetic acid as a sticky oil that was used without further purification in the following coupling reaction. MS (ESI): 480 (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-30593fc3263c41438412174659458c60
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

Loading…