Sodium Hydroxide → HCID 178460227, compound

HRID 1194906Notes

Reaction equation

HRID 1194906 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][C:15]([C@H:18]2[CH2:23][CH2:22][C@H:21]([CH3:24])[CH2:20][CH2:19]2)([CH3:17])[CH3:16])/[C:8]([O:10]CC)=[O:9])[N:6]=1.[OH-].[Na+]>C(O)C.O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][C:15]([C@H:18]2[CH2:23][CH2:22][C@H:21]([CH3:24])[CH2:20][CH2:19]2)([CH3:17])[CH3:16])/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 178472871HCID 178472871, compound

Product 1

HCID 178460227HCID 178460227, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Ethyl 2-(2-aminothiazol-4-yl)-(Z)-2-[1-(trans-4-methylcyclohexyl)-1-methylethoxyimino]acetate (630 mg, 1.78 mmol) in ethanol (14 ml) and water (2 ml) was treated with 1M NaOH (1.78 ml) and the mixture was stirred at room temperature for 5 days. The ethanol was removed by evaporation in vacuo and the residual mixture was treated with ethyl acetate (100 ml) and water (100 ml) and the pH was adjusted to 3.0. The aqueous layer was extracted with ethyl acetate (3×30 ml). The combined ethyl acetate layers were dried (MgSO4) and evaporated to leave the title compound (390 mg, 67%), νmax (KBr) 3290, 3120, 2942, 1724, 1616, 1447, 1380, and 985 cm-1 ; δH (250 MHz, (CD3)2SO), 0.84 (3H, d, J 6.4 Hz), 1.17 (6H, s), 0.7-1.9 (10 H, m), 6.78 (1H, s), 7.25 (2H, s), and 13.5 (1H, broad s).

Workup

  1. customThe ethanol was removed by evaporation in vacuo
  2. additionthe residual mixture was treated with ethyl acetate (100 ml) and water (100 ml)
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×30 ml)
  4. dry with materialThe combined ethyl acetate layers were dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-0f0e43ebaba540799dcc3e0cec1f3af3
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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