1-Naphthalenesulfonyl chloride → HCID 178453605, compound

HRID 50534

Reaction equation

HRID 50534 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([CH2:15][NH2:16])[CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)C(C)C)C.[C:27]1([S:37](Cl)(=[O:39])=[O:38])[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][CH:28]=1>CN(C)C=O>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C@H:9]1[CH2:10][CH2:11][C@H:12]([CH2:15][NH:16][S:37]([C:27]2[C:36]3[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=3)[CH:30]=[CH:29][CH:28]=2)(=[O:39])=[O:38])[CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 665601-Naphthalenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 178453600HCID 178453600, compound

Product 1

HCID 178453605HCID 178453605, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of trans- (4-aminomethyl-cyclohexylmethyl)-carbamic acid tert-butyl ester (17 g) and ethyldiisopropylamine (14.41 ml) in N,N-dimethylformamide (350 ml) is cooled to 0° C. and treated with a solution of naphthalene-1-sulfonylchloride (15.9 g) in N,N-dimethylformamide (100 ml). The reaction is stirred at ambient temperature for 2 h, concentrated in vacuo. The residue is taken up in dichloromethane, washed with a 0.5 N HCl solution, a saturated aqueous sodium carbonate solution and water, dried and concentrated. Crystallization from hexanes-ethyl acetate gives trans-(4-[ (naphthalene-1-sulfonylamino)-methyl]-cyclohexylmethyl)-carbamic acid tert-butyl ester as a white powder, melting at 199-200° C. Rf(A1) 0.42.

Workup

  1. concentrationconcentrated in vacuo
  2. washwashed with a 0.5 N HCl solution
  3. dry with materiala saturated aqueous sodium carbonate solution and water, dried
  4. concentrationconcentrated
  5. customCrystallization from hexanes-ethyl acetate

Sources & evidence

ORD record
ord-b868e4eaa1c24fd189d3b8cf6c59dfb9
Source dataset
uspto-grants-2004_03
Patent number
US06713265B1

Linked notes

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