Methanesulfonyl chloride → N-[cis-4-(Boc-amino)cyclohexyl]methanesulfonamide

HRID 590073Notes

Reaction equation

HRID 590073 reaction equation
[C:1]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([NH2:15])[CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:16][S:17](Cl)(=[O:19])=[O:18]>C(Cl)Cl>[CH3:16][S:17]([NH:15][CH:12]1[CH2:11][CH2:10][CH:9]([NH:8][C:1](=[O:2])[O:3][C:4]([CH3:7])([CH3:6])[CH3:5])[CH2:14][CH2:13]1)(=[O:19])=[O:18]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 178419079HCID 178419079, compound

Product 1

HCID 18348373N-[cis-4-(Boc-amino)cyclohexyl]methanesulfonamideYield 67.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The trans-N-boc-1,4-cyclohexanediamine (1.00 g, 4.67 mmol) was dissolved in DCM (50 mL). Next, TEA was added (1.301 mL, 9.33 mmol), followed by methanesulfonyl chloride (0.397 mL, 5.13 mmol). The reaction was allowed to stir at rt for 22 h. The reaction mixture was partitioned between DCM (100 mL) and water (25 mL). The phases were separated and the aqueous phase was extracted with DCM (50 mL). Combined organic layer was dried over MgSO4 for 20 h overnight. Filtered and evaporated to dryness to give the title compound of Step A as a solid (0.924 g). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.32 (s, 8H), 2.89 (s, 3H), 1.83-1.91 (m, 1H), 1.70-1.78 (m, 1H), 1.37 (s, 9H).

Workup

  1. additionNext, TEA was added (1.301 mL, 9.33 mmol)
  2. customThe reaction mixture was partitioned between DCM (100 mL) and water (25 mL)
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with DCM (50 mL)
  5. dry with materialCombined organic layer was dried over MgSO4 for 20 h overnight
  6. filtrationFiltered
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-7eea6ffb2dd8482b975362628c6ae57a
Source dataset
uspto-grants-2016_01
Patent number
US09233956B2

Reaction notes

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