Triethylamine → [4'-(Methanesulfonylamino-methyl)-biphenyl-3-yl]-carbamic acid tert-butyl ester

HRID 1665730Notes

Reaction equation

HRID 1665730 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:19]=[CH:18][C:17]([CH2:20][NH2:21])=[CH:16][CH:15]=2)[CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:3])[CH3:2].CCN(CC)CC.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>ClCCl>[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[CH:9]=[C:10]([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][NH:21][S:31]([CH3:30])(=[O:33])=[O:32])=[CH:18][CH:19]=2)[CH:11]=[CH:12][CH:13]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 59206790(4'-Aminomethyl-biphenyl-3-yl)-carbamic acid tert-butyl ester

Product 1

HCID 59206047[4'-(Methanesulfonylamino-methyl)-biphenyl-3-yl]-carbamic acid tert-butyl esterYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude (4′-aminomethyl-biphenyl-3-yl)-carbamic acid tert-butyl ester (8.2 g 27 mmol) and Et3N (4.2 g, 40 mmol) in dichloromethane (250 mL) was added dropwise MsCl (3.2 g, 27 mmol) at 0° C. The reaction mixture was stirred at this temperature for 30 min and was then washed with water and saturated aqueous NaCl solution, dried over Na2SO4, and concentrated to dryness. The residue was recrystallized with DCM/pet ether (1:3) to give [4′-(methanesulfonylamino-methyl)-biphenyl-3-yl]-carbamic acid tert-butyl ester (7.5 g, yield 73%). 1H NMR (300 MHz, CDCl3) δ 7.67 (s, 1 H), 7.58 (d, J=8.1 Hz, 2 H), 7.23-7.41 (m, 5 H), 6.57 (s, 1 H), 4.65-4.77 (m, 1 H), 4.35 (d, J=6 Hz, 2 H), 2.90 (s, 3 H), 1.53 (s, 9 H).

Workup

  1. washwas then washed with water and saturated aqueous NaCl solution
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated to dryness
  4. customThe residue was recrystallized with DCM/pet ether (1:3)

Sources & evidence

ORD record
ord-bd6611be5be74ff2be509081a774ef73
Source dataset
uspto-grants-2011_10
Patent number
US08039491B2

Reaction notes

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