Methanesulfonyl chloride → HCID 178454053, compound

HRID 2268421Notes

Reaction equation

HRID 2268421 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:9][CH2:8]1.C(N(C(C)C)C(C)C)C>ClCCl>[CH3:1][S:2]([NH:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:18])([CH3:17])[CH3:19])[CH2:9][CH2:8]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178419079HCID 178419079, compound

Product 1

HCID 178454053HCID 178454053, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.56 g, 4.7 mmol) was added to a stirred solution of tert-butyl trans-4-aminocyclohexylcarbamate (J. Org. Chem. 8811, 61, 1996) (1.0 g, 4.7 mmol) and N-ethyl-N-isopropyl-2-propanamine (0.67 g, 0.52 mmol) in dichloromethane (30 ml). The reaction mixture was stirred for 30 min at room temperature and then partitioned between ethyl acetate (300 ml) and water (100 ml). The organic layer was washed twice with 1 molar aqueous citric acid solution and then with a saturated aqueous solution of sodium hydrogen carbonate, dried with anhydrous sodium sulfate and the solvent removed under reduced pressure to give a residue that was triturated with diethyl ether to give the title compound (0.99 g) as a white solid.

Workup

  1. custompartitioned between ethyl acetate (300 ml) and water (100 ml)
  2. washThe organic layer was washed twice with 1 molar aqueous citric acid solution
  3. dry with materialwith a saturated aqueous solution of sodium hydrogen carbonate, dried with anhydrous sodium sulfate
  4. customthe solvent removed under reduced pressure
  5. customto give a residue that
  6. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-84ced4868db245158f2dc5322e413d6c
Source dataset
uspto-grants-2001_12
Patent number
US06326359B1

Reaction notes

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