Water → (2Z)-2-[2-(diethoxyphosphorylamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetic acid

HRID 1461714Notes

Reaction equation

HRID 1461714 reaction equation
[CH2:1]([O:3][P:4]([NH:9][C:10]1[S:11][CH:12]=[C:13](/[C:15](=[N:21]/[O:22][CH3:23])/[C:16]([O:18]CC)=[O:17])[N:14]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[OH-].[Na+].O>O1CCOCC1>[CH2:7]([O:6][P:4]([NH:9][C:10]1[S:11][CH:12]=[C:13](/[C:15](=[N:21]/[O:22][CH3:23])/[C:16]([OH:18])=[O:17])[N:14]=1)([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 178472870ethyl (2Z)-2-[2-(diethoxyphosphorylamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetate

Product 1

HCID 15028031(2Z)-2-[2-(diethoxyphosphorylamino)-1,3-thiazol-4-yl]-2-methoxyiminoacetic acidYield 59.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 8.4 g (0.023 mol) (Z)-2-[(diethoxyphosphinyl)amino]-α-(methoxyimino)-4-thiazoleacetic acid, ethyl ester, 9.25 ml (0.046 mol) 5N sodium hydroxide, 30 ml water, and 50 ml dioxane was stirred at room temperature for 18 hours. The solvent was evaporated, 30 ml of 50% saturated sodium chloride was added, the pH was adjusted to 4.5, and 3×30 ml ethyl acetate was added. The aqueous layer was then adjusted to pH 2.5, and extraction with ethyl acetate followed by evaporation yielded 4.6 g of a yellow oil; MS ((+) FAB), 338 (M+H); NMR (300 MHz, DCCl3) δ 1.36 (2t, 6, OCH2CH3), 4.01 (s, 3, OCH3), 4.18 (m, 4, OCH2), 7.10 (s, 1, thiazole H).

Workup

  1. customThe solvent was evaporated
  2. addition30 ml of 50% saturated sodium chloride was added
  3. additionwas added
  4. extractionThe aqueous layer was then adjusted to pH 2.5, and extraction with ethyl acetate
  5. customfollowed by evaporation

Sources & evidence

ORD record
ord-766ec4fd4674483f8cc235975fdf684b
Source dataset
uspto-grants-1991_12
Patent number
US05077282

Reaction notes

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