Sodium Bicarbonate → N-(2-(2-(4-Hydroxy-4-(thiophen-2-yl)piperidin-1-yl)-2-oxoethoxy)ethyl)-4-methoxy-N,2,6-trimethylphenylsulfonamide

HRID 2041093Notes

Reaction equation

HRID 2041093 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH3:9])[C:6]([S:10]([N:13]([CH2:15][CH2:16][O:17][CH2:18][C:19]([OH:21])=O)[CH3:14])(=[O:12])=[O:11])=[C:5]([CH3:22])[CH:4]=1.[S:23]1[CH:27]=[CH:26][CH:25]=[C:24]1[C:28]1([OH:34])[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[OH:34][C:28]1([C:24]2[S:23][CH:27]=[CH:26][CH:25]=2)[CH2:29][CH2:30][N:31]([C:19](=[O:21])[CH2:18][O:17][CH2:16][CH2:15][N:13]([CH3:14])[S:10]([C:6]2[C:5]([CH3:22])=[CH:4][C:3]([O:2][CH3:1])=[CH:8][C:7]=2[CH3:9])(=[O:11])=[O:12])[CH2:32][CH2:33]1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 14441129HCID 14441129, compoundHCID 46870354{2-[(4-methoxy-2,6-dimethyl-benzenesulfonyl)-methyl-amino]-ethoxy}acetic Acid

Product 1

HCID 59820102N-(2-(2-(4-Hydroxy-4-(thiophen-2-yl)piperidin-1-yl)-2-oxoethoxy)ethyl)-4-methoxy-N,2,6-trimethylphenylsulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N′-Carbonyldiimidazole (77 mg, 0.475 mmol) was added to a solution of 2-(2-(4-methoxy-N,2,6-trimethylphenylsulfonamido)-ethoxy)acetic acid (acid unit S2) (150 mg, 0.453 mmol) in methylene chloride (7 ml) and the mixture was stirred for 1 h at room temperature. A solution of 4-(thiophen-2-yl)piperidin-4-ol (A7) (82 mg, 0.453 mmol) in methylene chloride (3 ml) was subsequently added and the reaction mixture was stirred for 15 h at room temperature. Thereafter, saturated sodium bicarbonate solution (10 ml) was added to the reaction mixture and the aqueous phase was subsequently extracted with methylene chloride (20 ml). The combined organic phases were extracted with saturated sodium chloride solution (10 ml), dried with sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography with ethyl acetate/methanol/ammonia solution (25% aq.) (100:10:1).

Workup

  1. stirringthe reaction mixture was stirred for 15 h at room temperature
  2. extractionthe aqueous phase was subsequently extracted with methylene chloride (20 ml)
  3. extractionThe combined organic phases were extracted with saturated sodium chloride solution (10 ml)
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography with ethyl acetate/methanol/ammonia solution (25% aq.) (100:10:1)

Sources & evidence

ORD record
ord-c6d6a7279632448a8cd8464760c8aaee
Source dataset
uspto-grants-2013_11
Patent number
US08580965B2

Reaction notes

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