Potassium Hydroxide → HCID 66815878, compound

HRID 1754918Notes

Reaction equation

HRID 1754918 reaction equation
[OH-].[K+].C([O:6][CH2:7][C@@H:8]([O:47]C(=O)C)[CH2:9][N:10](C(=O)C)[C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][S:19]([N:22]2[CH2:42][CH2:41][C:25]3([N:29]=[C:28]([C:30]4[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=4)[NH:27][C:26]3=[O:40])[CH2:24][CH2:23]2)(=[O:21])=[O:20])=[C:13]([CH3:43])[CH:12]=1)(=O)C>CO>[OH:47][C@H:8]([CH2:7][OH:6])[CH2:9][NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][S:19]([N:22]2[CH2:23][CH2:24][C:25]3([N:29]=[C:28]([C:30]4[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=4)[NH:27][C:26]3=[O:40])[CH2:41][CH2:42]2)(=[O:21])=[O:20])=[C:13]([CH3:43])[CH:12]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 66817284HCID 66817284, compound

Product 1

HCID 66815878HCID 66815878, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

A 1.2 M aqueous KOH solution (0.5 mL) was added to a solution of acetic acid (S)-1-acetoxymethyl-2-[acetyl-(3-methyl-4-{2-[4-oxo-2-(4-trifluoromethyl-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-ene-8-sulfonyl]-ethyl}-phenyl)-amino]-ethyl ester (40.8 mg, 0.0587 mmol) in MeOH (3 mL). The reaction mixture was stirred at 50° C. for 1.5 hours and then cooled to room temperature. Dowex 50W×4 (237.6 mg) was added. The mixture was further stirred at room temperature for two hours and then filtered, and the organic layer was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (CH2Cl2/MeOH=10/1) to give 8-{2-[4-((S)-2,3-dihydroxy-propylamino)-2-methyl-phenyl]-ethanesulfonyl}-2-(4-trifluoromethyl-phenyl)-1,3,8-triaza-spiro[4.5]dec-1-en-4-one as a white powder (30.3 mg, 91%).

Workup

  1. temperaturecooled to room temperature
  2. stirringThe mixture was further stirred at room temperature for two hours
  3. filtrationfiltered
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (CH2Cl2/MeOH=10/1)

Sources & evidence

ORD record
ord-d012af5c4b1f4591b6d39aa7003395ea
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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