Water → HCID 57595410, compound

HRID 1786015Notes

Reaction equation

HRID 1786015 reaction equation
[CH3:1][S:2]([N:5](S(C)(=O)=O)[C:6]1[CH:35]=[CH:34][C:9]([C:10]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C@H:15]([N:22]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[C:23](=[O:25])[CH3:24])[CH2:14][C@@H:13]2[CH3:33])=[O:11])=[CH:8][CH:7]=1)(=[O:4])=[O:3].[OH-].[Na+].O.C(=O)(O)[O-].[Na+]>O1CCCC1>[Cl:32][C:29]1[CH:30]=[CH:31][C:26]([N:22]([C@H:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[N:12]([C:10](=[O:11])[C:9]3[CH:34]=[CH:35][C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:7][CH:8]=3)[C@@H:13]([CH3:33])[CH2:14]2)[C:23](=[O:25])[CH3:24])=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 68920922HCID 68920922, compound

Product 1

HCID 57595410HCID 57595410, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-((2S,4R)-1-{4-[bis(methylsulfonyl)amino]benzoyl}-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)-N-(4-chlorophenyl)acetamide (259 mg, 0.44 mmol) in tetrahydrofuran (5.0 mL) at room temperature was added 1.0 M sodium hydroxide (0.880 mL, 0.88 mmol). The reaction was stirred at room temperature for 2 days. The resulting reaction mixture was poured into a 1:1 mixture of water and saturated sodium bicarbonate (25 mL) and extracted with ethyl acetate (1×25 mL). The aqueous layer was neutralized via addition of 1N HCl to pH ˜8 and extracted with ethyl acetate (2×25 mL). The combined organic layers were washed once with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure to afford N-(4-chlorophenyl)-N-((2S,4R)-2-methyl-1-{4-[(methylsulfonyl)amino]benzoyl}-1,2,3,4-tetrahydroquinolin-4-yl)acetamide (190 mg, 76%) as a light-yellow, foamy solid.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with ethyl acetate (1×25 mL)
  3. additionThe aqueous layer was neutralized via addition of 1N HCl to pH ˜8
  4. extractionextracted with ethyl acetate (2×25 mL)
  5. washThe combined organic layers were washed once with brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-61d2f884d424442d8dd39ecaf517e5d6
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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