Water → HCID 14865027, compound

HRID 1194871Notes

Reaction equation

HRID 1194871 reaction equation
[CH:1]1([CH2:4][O:5]/[N:6]=[C:7](/[C:13]2[N:14]=[C:15]([NH:18]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[S:16][CH:17]=2)\[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3][CH2:2]1.O>C(O)=O>[CH2:11]([O:10][C:8](=[O:9])/[C:7](/[C:13]1[N:14]=[C:15]([NH2:18])[S:16][CH:17]=1)=[N:6]\[O:5][CH2:4][CH:1]1[CH2:2][CH2:3]1)[CH3:12]

Participants

4

Reactant 2

HCID 962WaterHCID 13269245HCID 13269245, compound

Product 1

HCID 14865027HCID 14865027, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Ethyl (Z)-2-cyclopropylmethoxyimino-2-(2-tritylaminothiazol-4-yl)acetate (2.39 g) was dissolved in 98% formic acid (18.7 ml), water (5.6 ml) was added, and the mixture vigorously stirred. After 6 h the solvents were evaporated, toluene added to the residue and the process repeated. This was done twice more. The residual solid was chromatographed on silica to give the title compound as a white solid (1.17 g), νmax (Nujol) 3440, 3250, 3120, 1720, and 1620 cm-1 ; δH (CDCl3) inter alia 1.35 (3H, t, J 7 Hz), 4.0 (2H, d, J 7 Hz), 4.37 (2H, q, J 7 Hz), 5.4 (2H, broad s, exch. D2O), and 6.67 (1H, s).

Workup

  1. customAfter 6 h the solvents were evaporated
  2. additiontoluene added to the residue
  3. customThe residual solid was chromatographed on silica

Sources & evidence

ORD record
ord-7952a0d63317461b9b87aa4b7f48ac6e
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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