Potassium Hydroxide → (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[2-methyl-1-oxo-1-(1-tritylpiperazin-2-yl)propan-2-yl]oxyiminoacetic acid

HRID 482941Notes

Reaction equation

HRID 482941 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:12]/[O:13][C:14]([CH3:43])([CH3:42])[C:15](=[O:41])[CH:16]2[CH2:21][NH:20][CH2:19][CH2:18][N:17]2[C:22]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)/[C:8]([O:10]C)=[O:9])[N:6]=1.[OH-].[K+]>C(O)C.O>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:12]/[O:13][C:14]([CH3:43])([CH3:42])[C:15](=[O:41])[CH:16]2[CH2:21][NH:20][CH2:19][CH2:18][N:17]2[C:22]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 178501735HCID 178501735, compound

Product 1

HCID 88675838(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[2-methyl-1-oxo-1-(1-tritylpiperazin-2-yl)propan-2-yl]oxyiminoacetic acidYield 43.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

(Z)-2-Amino-α-[[1,1-dimethyl-2-oxo-2-(N-tritylpiperazinyl)ethoxy]imino]-4-thiazoleacetic acid, methyl ester (4.03 g, 6.75 mmol) was suspended in a solution of 0.90 g of potassium hydroxide in ethanol (22.5 ml) and water (1.8 ml), and stirred overnight at room temperature. The reaction was then heated to 60° C. for 30 minutes. Upon cooling to room temperature, water (22.5 ml) was added, and the reaction mixture was filtered through Celite. The filtrate was then acidified to pH 3 with 1N hydrochloride acid while cooling in ice, and the precipitate that formed was isolated by filtration. The precipitate was washed with water, ether and acetonitrile to yield 1.71 g of the title compound.

Workup

  1. temperatureThe reaction was then heated to 60° C. for 30 minutes
  2. temperatureUpon cooling to room temperature
  3. filtrationthe reaction mixture was filtered through Celite
  4. temperaturewhile cooling in ice
  5. customthe precipitate that formed
  6. customwas isolated by filtration
  7. washThe precipitate was washed with water, ether and acetonitrile

Sources & evidence

ORD record
ord-1ca3e90eaa0e424f8199138520ac18ab
Source dataset
uspto-grants-1986_03
Patent number
US04576749

Reaction notes

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