Methanol → HCID 58625126, compound

HRID 390231Notes

Reaction equation

HRID 390231 reaction equation
[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[CH:15]([C:17]1[CH:18]=[C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][CH2:33][NH:34][S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)(=[O:37])=[O:36])[CH:20]=[CH:21][C:22]=1[N+:23]([O-:25])=[O:24])=O.[CH2:44]([NH2:47])[CH2:45][CH3:46].CO>ClCCCl>[N+:23]([C:22]1[CH:21]=[CH:20][C:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[CH2:32][CH2:33][NH:34][S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)(=[O:36])=[O:37])=[CH:18][C:17]=1[CH2:15][NH:47][CH2:44][CH2:45][CH3:46])([O-:25])=[O:24]

Participants

6

Reactant 4

HCID 887MethanolHCID 7852PropylamineHCID 5049666Sodium triacetoxyborohydride2×HCID 58625166HCID 58625166, compound

Product 1

HCID 58625126HCID 58625126, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

NaBH(OAc)3 (0.0031 mol) was added to a mixture of N-[2-(3′-formyl-4′-nitro-biphenyl-2-yl)-ethyl]-benzenesulfonamide (0.0021 mol) and propylamine (0.0023 mol) in DCE (2 mL), and the reaction mixture was stirred overnight under N2. The excess of NaBH(OAc)3 was decomposed with CH3OH, and the solvent was evaporated. The residue was purified by Biotage column chromatography (eluent: 95:5 CH2Cl2:CH3OH). The purest product fractions were collected and then the solvent was evaporated and co-evaporated with toluene to yield the title compound as a residue.

Workup

  1. customthe solvent was evaporated
  2. customThe residue was purified by Biotage column chromatography (eluent: 95:5 CH2Cl2:CH3OH)
  3. customThe purest product fractions were collected
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-87a72cd67dbb409ca8490e916044f784
Source dataset
uspto-grants-2013_02
Patent number
US08383637B2

Reaction notes

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