Ethyl Acetate → HCID 88627177, compound

HRID 1194912Notes

Reaction equation

HRID 1194912 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][C@@H:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]2[O:21][CH3:22])/[C:8]([O:10]CC)=[O:9])[N:6]=1.[OH-].[Na+].C(OCC)(=O)C>C(O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5](/[C:7](=[N:13]/[O:14][C@@H:15]2[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]2[O:21][CH3:22])/[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 88627012HCID 88627012, compound

Product 1

HCID 88627177HCID 88627177, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 2-(2-aminothiazol-4-yl)-(Z)-2-(trans-2-methoxycyclohexyloxyimino)acetate (1.79 g) was hydrolysed with IM sodium hydroxide (10.75 ml) in ethanol (20 ml) as described in Example 4e. After acidification of the aqueous phase to pH 2-3 the water was removed under reduced pressure. The residue was extracted with hot ethanol and concentrated to dryness to give a brown foam. Trituration with ethyl acetate gave the title compound as a buff coloured solid (0.904 g). νmax (KBr) 3302, 3207, 1628, 1534, and 1450 cm-1 ; δH ((CD3)2SO) inter alia 1.00-2.00 (8H, m), 3.00-3.33 (4H, m and s), 3.90-4.30 (1H, m), 6.87 (1H, s), and 7.28 (3H, br. s). [Mass spectrum: +ve ion (thioglycerol) MH+ (300), MNa+ (322)].

Workup

  1. customAfter acidification of the aqueous phase to pH 2-3 the water was removed under reduced pressure
  2. extractionThe residue was extracted with hot ethanol
  3. concentrationconcentrated to dryness
  4. customto give a brown foam

Sources & evidence

ORD record
ord-47d8a4af65d042f79067fee8da71f708
Source dataset
uspto-grants-1989_03
Patent number
US04816452

Reaction notes

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