Hydrochloric Acid → HCID 58882900, compound

HRID 2364135Notes

Reaction equation

HRID 2364135 reaction equation
CC[O-].[Na+].[CH2:5]([C:12]1[CH:13]=[C:14]([N:23]([C:35](=[O:42])[CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:24][C:25]2[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=2)[C:15]([C:18]([O:20]CC)=O)=[N:16][CH:17]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl>CCO>[CH2:5]([C:12]1[CH:13]=[C:14]2[C:15]([C:18]([OH:20])=[C:36]([C:37]([O:39][CH2:40][CH3:41])=[O:38])[C:35](=[O:42])[N:23]2[CH2:24][C:25]2[CH:26]=[CH:27][C:28]([S:31]([CH3:34])(=[O:32])=[O:33])=[CH:29][CH:30]=2)=[N:16][CH:17]=1)[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2723922Sodium ethoxideHCID 58882904HCID 58882904, compound

Product 1

HCID 58882900HCID 58882900, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 1M NaOEt in EtOH (2.5 mL, 2.5 mmol) was added dropwise to a solution of ethyl 5-benzyl-3-{(3-ethoxy-3-oxopropanoyl)[4-(methylsulfonyl)benzyl]-amino}-pyridine-2-carboxylate (690 mg, 1.26 mmol) in EtOH (6 mL). The mixture was stirred at rt for 30 min, neutralized with 1M HCl (2.5 mL) and the resulting precipitate was collected by filtration washing with 1:1 water/EtOH. This procedure afforded the product as an off-white solid: 1H NMR (CDCl3) δ 14.07 (1H, br s), 8.56 (1H, s), 7.79 (2H, d, J=8 Hz), 7.30 (3H, m), 7.19 (2H, d, J=8 Hz), 7.02 (3H, m), 5.40 (2H, br s), 4.53 (2H, q, J=7 Hz), 4.04 (2H, s), 3.01 (3H, s), 1.48 (3H, s); HRMS calcd for C26H24N2O6S+H+: 493.1433. Found: 493.1422.

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashing with 1:1 water/EtOH

Sources & evidence

ORD record
ord-84118016b7b34aa986f5160b90269471
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

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