Methanol → 2-Cyclopropyloxyimino-2-(5-tritylamino-1,2,4-thiadiazol-3-yl)acetic acid

HRID 1074345Notes

Reaction equation

HRID 1074345 reaction equation
[CH:1]1([O:4][N:5]=[C:6]([C:12]2[N:16]=[C:15]([NH:17][C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:14][N:13]=2)[C:7]([O:9]CC)=[O:8])[CH2:3][CH2:2]1.CO.[OH-].[Na+]>O1CCCC1>[CH:1]1([O:4][N:5]=[C:6]([C:12]2[N:16]=[C:15]([NH:17][C:18]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[S:14][N:13]=2)[C:7]([OH:9])=[O:8])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 53744924Ethyl 2-cyclopropyloxyimino-2-(5-tritylamino-1,2,4-thiadiazol-3-yl)acetate

Product 1

HCID 541856782-Cyclopropyloxyimino-2-(5-tritylamino-1,2,4-thiadiazol-3-yl)acetic acidYield 74.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 2-cyclopropyloxyimino-2-(5-tritylamino-1,2,4-thiadiazol-3-yl)acetate (syn isomer)(11 g) in a mixture of tetrahydrofuran (72 ml), methanol (72 ml) and 2N sodium hydroxide (72 ml) was stirred at ambient temperature overnight. The mixture was concentrated in vacuo. The residue was dissolved in a mixture of ethyl acetate and water and adjusted to pH 2 with 3N hydrochloric acid. The organic layer was separated, washed with water and saturated aqueous solution of sodium chloride, dried over magnesium sulfate, concentrated in vacuo, and triturated with petroleum ether to give 2-cyclopropyloxyimino-2-(5-tritylamino-1,2,4-thiadiazol-3-yl)acetic acid (syn isomer) (7.75 g) as a solid.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionThe residue was dissolved in a mixture of ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with water and saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customtriturated with petroleum ether

Sources & evidence

ORD record
ord-63962b0d8e35483aab0e4bb715211c15
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

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