Sodium triacetoxyborohydride → 2-(5-Benzoyl-2-nitro-benzylamino)-ethanesulfonic acid cyclohexyl-methyl-amide

HRID 390269Notes

Reaction equation

HRID 390269 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH:15]1([N:21]([CH3:28])[S:22]([CH2:25][CH2:26][NH2:27])(=[O:24])=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[C:29]([C:37]1[CH:38]=[CH:39][C:40]([N+:45]([O-:47])=[O:46])=[C:41]([CH:44]=1)[CH:42]=O)(=[O:36])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>ClCCCl>[CH:15]1([N:21]([CH3:28])[S:22]([CH2:25][CH2:26][NH:27][CH2:42][C:41]2[CH:44]=[C:37]([C:29](=[O:36])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:38]=[CH:39][C:40]=2[N+:45]([O-:47])=[O:46])(=[O:24])=[O:23])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 198160555-Benzoyl-2-nitrobenzaldehydeHCID 431759162-amino-N-cyclohexyl-N-methylethanesulfonamide

Product 1

HCID 586251122-(5-Benzoyl-2-nitro-benzylamino)-ethanesulfonic acid cyclohexyl-methyl-amide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

NaBH(OAc)3 (0.014 mol) was added to a mixture of 2-amino-ethanesulfonic acid cyclohexyl-methyl-amide (0.0091 mol) and 5-benzoyl-2-nitro-benzaldehyde (0.0091 mol) in DCE (150 mL). The reaction mixture was then stirred overnight at room temperature and then washed with saturated NaHCO3 solution. The organic layer was separated, dried (MgSO4), and filtered, and the solvent was evaporated. The residue was purified by column chromatography (eluent: 100% CH2Cl2). The purest product fractions were collected and the solvent was evaporated to yield the title compound as a residue.

Workup

  1. washwashed with saturated NaHCO3 solution
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated
  6. customThe residue was purified by column chromatography (eluent: 100% CH2Cl2)
  7. customThe purest product fractions were collected
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-7840cd1ae4ee435494ac3c7849aaa536
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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