Pyridine → Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-(methylsulfonamidomethyl)phenoxy)benzoate

HRID 453543Notes

Reaction equation

HRID 453543 reaction equation
[NH2:1][CH2:2][C:3]1[CH:19]=[C:18]([CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:17]=[CH:16][C:4]=1[O:5][C:6]1[CH:15]=[CH:14][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:8][CH:7]=1.N1C=CC=CC=1.[CH3:34][S:35](Cl)(=[O:37])=[O:36]>ClCCl.C(OCC)(=O)C.Cl>[C:24]([O:23][C:21](=[O:22])[CH2:20][C:18]1[CH:17]=[CH:16][C:4]([O:5][C:6]2[CH:7]=[CH:8][C:9]([C:10]([O:12][CH3:13])=[O:11])=[CH:14][CH:15]=2)=[C:3]([CH2:2][NH:1][S:35]([CH3:34])(=[O:37])=[O:36])[CH:19]=1)([CH3:27])([CH3:26])[CH3:25]

Participants

7

Reactant 3

HCID 1049Pyridine2×HCID 31297Methanesulfonyl chloride2×HCID 68464831Methyl 4-(2-(aminomethyl)-4-(2-tert-butoxy-2-oxoethyl)phenoxy)benzoate

Product 1

HCID 68468952Methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-(methylsulfonamidomethyl)phenoxy)benzoateYield 90.2%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of the methyl 4-(2-(aminomethyl)-4-(2-tert-butoxy-2-oxoethyl)phenoxy)benzoate (690 mg, 1.86 mmol) in dichloromethane (6 ml) was added pyridine (225 μL, 2.78 mmol) followed by methanesulfonyl chloride (287 μL, 3.71 mmol). The reaction was stirred at ambient temperature for 4 hours, after which time additional pyridine (1.5 eq) and methanesulfonyl chloride (2 eq) were added. The reaction was stirred for an additional hour and then diluted with ethyl acetate and 1M HCl. The aqueous layer was extracted with ethyl acetate and the combined organics washed with brine and dried over MgSO4. The crude product was then purified on the Biotage Horizon (40+M, 5% to 75% B:ethyl acetate) to give methyl 4-(4-(2-tert-butoxy-2-oxoethyl)-2-(methylsulfonamidomethyl)phenoxy)benzoate (0.754 g).

Workup

  1. stirringThe reaction was stirred for an additional hour
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washthe combined organics washed with brine
  4. dry with materialdried over MgSO4
  5. customThe crude product was then purified on the Biotage Horizon (40+M, 5% to 75% B:ethyl acetate)

Sources & evidence

ORD record
ord-ca88c71b0cc54e29ad1a99888cc7a466
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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