Benzylamine → HCID 58121065, compound

HRID 1186689Notes

Reaction equation

HRID 1186689 reaction equation
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[S:17]([C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23])(=[O:19])=[O:18]>C(Cl)Cl>[CH2:1]([NH:8][S:17]([C:20]1[CH:29]=[CH:28][CH:27]=[CH:26][C:21]=1[C:22]([O:24][CH3:25])=[O:23])(=[O:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl ester

Product 1

HCID 58121065HCID 58121065, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of benzylamine 42 (0.140 mL, 1.278 mmol) in DCM (2.557 mL) was added triethylamine (0.535 mL, 3.84 mmol) and methyl 2-(chlorosulfonyl)benzoate 41 (300 mg, 1.278 mmol) and the resulting colorless solution was stirred at rt for 20 h. The reaction mixture was partitioned between DCM and H2O. The organic layer was washed with 1M HCl, saturated NaHCO3, and brine, dried over MgSO4, filtered and concentrated. The crude mixture was purified by Biotage using EtOAc/Hex ((20:80 to 40:60); 25+S column) to afford compound 43 (49 mgs, 13% yield) as a colorless oil. LRMS (ESI): (calc.) 305.07 (found) 306.2 (MH)+

Workup

  1. customThe reaction mixture was partitioned between DCM and H2O
  2. washThe organic layer was washed with 1M HCl, saturated NaHCO3, and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude mixture was purified by Biotage

Sources & evidence

ORD record
ord-4df21b395c384b95abf06be1f12232ee
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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