Sodium Hydroxide → HCID 21186254, compound

HRID 1384208Notes

Reaction equation

HRID 1384208 reaction equation
[OH-].[Na+].C(OC([N:10]([C:33]1[C:38]([O:39][CH3:40])=[N:37][C:36]([CH3:41])=[CH:35][N:34]=1)[S:11]([C:14]1[C:15]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]([C:29]([O:31]C)=[O:30])[CH3:28])=[CH:22][CH:21]=2)=[N:16][CH:17]=[CH:18][CH:19]=1)(=[O:13])=[O:12])=O)C(C)C>CO.C(COC)OC>[C:29]([CH:27]([O:26][C:23]1[CH:24]=[CH:25][C:20]([C:15]2[C:14]([S:11]([NH:10][C:33]3[C:38]([O:39][CH3:40])=[N:37][C:36]([CH3:41])=[CH:35][N:34]=3)(=[O:13])=[O:12])=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:21][CH:22]=1)[CH3:28])([OH:31])=[O:30]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21186226HCID 21186226, compound

Product 1

HCID 21186254HCID 21186254, compoundYield 40.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2M Sodium hydroxide solution (1 ml) was added to a solution of N-(isobutoxycarbonyl)-2-(4-[1-(methoxycarbonyl)ethoxy]phenyl)-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.302 g) in methanol (5 ml) and dimethoxyethane (5 ml) and the solution was stirred for 3 days. Volatile material was removed by evaporation and the residue was dissolved in water (15 ml). The solution was washed with ethyl acetate (2×15 ml) and acidified to pH3 with 6M hydrochloric acid. The mixture was extracted with ethyl acetate (2×10 ml) and the extracts were re-extracted with saturated sodium bicarbonate solution (2×10 ml). The aqueous solution was acidified with 2M hydrochloric acid and extracted with ethyl acetate (2×10 ml). The extracts were washed with water (10 ml) and dried (MgSO4). Volatile material was removed by evaporation and the residue was recrystallised from ethyl acetate to give 2-[4-(1-carboxyethoxy)phenyl]-N-(3-methoxy-5-methylpyrazin-2-yl)pyridine-3-sulphonamide (0.098 g), m.p. 149-151 ° C.; microanalysis found: C, 53.6; H, 4.9; N, 11.7%; C18H18N4O6S.02C4H8O2 requires C, 5.41; H, 4.7; N, 12.1%.

Workup

  1. customVolatile material was removed by evaporation
  2. dissolutionthe residue was dissolved in water (15 ml)
  3. washThe solution was washed with ethyl acetate (2×15 ml)
  4. extractionThe mixture was extracted with ethyl acetate (2×10 ml)
  5. extractionthe extracts were re-extracted with saturated sodium bicarbonate solution (2×10 ml)
  6. extractionextracted with ethyl acetate (2×10 ml)
  7. washThe extracts were washed with water (10 ml)
  8. dry with materialdried (MgSO4)
  9. customVolatile material was removed by evaporation
  10. customthe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-639fdd2c58f14609a426838a121cc945
Source dataset
uspto-grants-2001_07
Patent number
US06258817B1

Reaction notes

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