Sodium Hydroxide → HCID 86742228, compound

HRID 580222Notes

Reaction equation

HRID 580222 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][N:12]=[C:11]([C:14](=[N:19][O:20][CH:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[C:15]([O:17]C)=[O:16])[N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C:9]1[S:13][N:12]=[C:11]([C:14](=[N:19][O:20][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25]2)[C:15]([OH:17])=[O:16])[N:10]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86742229HCID 86742229, compound

Product 1

HCID 86742228HCID 86742228, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 500 mg (1.34 mmoles) of methyl 2-(5-t-butoxycarbonylamino-1,2,4-thiadiazol-3-yl)-2-cyclopentyloxyiminoacetate and 2N NaOH solution (2 ml, 4 mmoles) in 15 ml of CH3OH was refluxed for 30 minutes. The reaction mixture was evaporated and 10 ml of ethyl acetate-H2O (1:1) was added to the solution. The water layer was separated, acidified to pH 2 with 6N HCl and extracted with ethyl acetate (10 ml×2). The organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure to give 377 mg (78%) of the title compound. Mp. 185° C. (dec.).

Workup

  1. customThe reaction mixture was evaporated
  2. addition10 ml of ethyl acetate-H2O (1:1) was added to the solution
  3. customThe water layer was separated
  4. extractionextracted with ethyl acetate (10 ml×2)
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b4222f3790d541d2a0888a8f90de5626
Source dataset
uspto-grants-1988_06
Patent number
US04751295

Reaction notes

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