Pyridine → Carbamic acid, [2-[4-[(phenylsulfonyl)amino]phenoxy]ethyl]-, 1,1-dimethylethyl ester

HRID 2399883Notes

Reaction equation

HRID 2399883 reaction equation
[CH3:1][C:2]([O:5][C:6](=[O:18])[NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([NH2:17])=[CH:13][CH:12]=1)([CH3:4])[CH3:3].N1C=CC=CC=1.[C:25]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[CH3:4][C:2]([CH3:1])([O:5][C:6]([NH:7][CH2:8][CH2:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([NH:17][S:31]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)(=[O:33])=[O:32])=[CH:15][CH:16]=1)=[O:18])[CH3:3]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 18173954tert-Butyl [2-(4-aminophenoxy)ethyl]carbamate

Product 1

HCID 19385031Carbamic acid, [2-[4-[(phenylsulfonyl)amino]phenoxy]ethyl]-, 1,1-dimethylethyl esterYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 314 mg(1.246 mmole) of t-BOC amine from Example 216 in 10 mL of methylene chloride was added pyridine (147 mg, 1.869 mmol, 1.5 eq) followed by benzenesulfonyl chloride (242 mg, 1.370 mmol, 1.1 eq) at room temperature. The reaction mixture was stirred at room temperature overnight and then partitioned between water and chloroform. The organic layer was separated and washed with 1N hydrochloric acid, water and brine and then dried over anhydrous sodium sulfate. The solution was filtered, concentrated and the residue was purified by flash colunto chromatography (eluant 2:1 hexanes/ethyl acetate) to give 248 mg (51%) of the product: 1H NMR (200 MHz, CDCl3) δ8.01 (d, 1H, J=8Hz), 7.67 (d, 2H, J=8Hz), 6.92 (d, 2H, J=9Hz), 6.72 (s, 1H, N-H), 6.70 (d, 2H, J=9Hz), 4.90 (bs, 1H, N-H), 3.89 (t, 2H, J=5.0Hz), 3.40 (q, 2H, J=5.0Hz), 1.40 (s, 9H).

Workup

  1. custompartitioned between water and chloroform
  2. customThe organic layer was separated
  3. washwashed with 1N hydrochloric acid, water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe solution was filtered
  6. concentrationconcentrated
  7. customthe residue was purified by flash colunto chromatography (eluant 2:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-175853e260ec48a0adcd6f5eaec785bc
Source dataset
uspto-grants-1995_09
Patent number
US05451677

Reaction notes

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