Acetaldehyde → HCID 178463347, compound

HRID 1944707Notes

Reaction equation

HRID 1944707 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([S:9]([NH:12][C@H:13]2[CH2:18][CH2:17][C@H:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]2)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH:23](=O)[CH3:24].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([S:9]([NH:12][C@H:13]2[CH2:14][CH2:15][C@H:16]([C:19]([O:21][CH3:22])=[O:20])[CH2:17][CH2:18]2)(=[O:10])=[O:11])=[CH:3][C:2]=1[NH:1][CH2:23][CH3:24]

Participants

6

Reactant 3

HCID 177AcetaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 178501249HCID 178501249, compound

Product 1

HCID 178463347HCID 178463347, compoundYield 64.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A round bottom flask was charged with methyl trans-4-(3-amino-4-chlorophenylsulfonamido)cyclohexamecarboxylate (Intermediate 10, 333 mg, 0.922 mmol) and acetaldehyde (52.1 μl, 0.922 mmol) followed by sodium triacetoxyborohydride (293 mg, 1.383 mmol) in DCE (9217 μl) and the reaction was stirred overnight. The reaction was diluted with DCM/sat'd NaHCO3, and the organic layer was separated and dried over MgSO4, then filtered and chromatographed on a Biotage 25S column to yield the title compound (224 mg, 0.598 mmol, 64.8% yield). Rf (50% EtOAc/heptane): sm=0.43; product=0.58. MS MH+=375.2

Workup

  1. customthe organic layer was separated
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. customchromatographed on a Biotage 25S column

Sources & evidence

ORD record
ord-2fd84e5f3f0e4bcc90e77328cb643641
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

Loading…