Hydrochloric Acid → 2-(2-Formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetic acid

HRID 745378Notes

Reaction equation

HRID 745378 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][CH2:16][NH2:17])[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2].C(=O)(O)[O-].[Na+].Cl.C1(C(=N[O:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=O)C#N)C=CC=CC=1>O.O1CCCC1.C(N(CC)CC)C>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:13][O:14][CH2:15][CH2:16][NH:17][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:34])[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 516892Sodium BicarbonateHCID 543766712-(2-Aminoethoxyimino)-2-(2-formamidothiazol-4-yl)acetic acid

Product 1

HCID 540828852-(2-Formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetic acidYield 36%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 2-(2-formamidothiazol-4-yl)-2-(2-aminoethoxyimino)acetic acid (syn isomer, 0.80 g.) and triethylamine (0.45 g.), in a solution of a saturated aqueous solution of sodium bicarbonate (4 ml.), tetrahydrofuran (35 ml.) and water (25 ml.) was adjusted to pH 8.5 with hydrochloric acid. 2-Phenyl-2-(tert-butoxycarbonyloxyimino)acetonitrile (0.77 g.) was added to the stirred solution and stirred at room temperature for 3 hours. After distilling off tetrahydrofuran from the resultant solution, the aqueous solution was washed with diethyl ether, and adjusted to pH 1.5 with 85% phosphoric acid. The solution was extracted with ethyl acetate (50 ml.), and the extract was washed with a saturated aqueous solution of sodium chloride (10 ml.), dried over magnesium sulfate and concentrated under reduced pressure to give 2-(2-formamidothiazol-4-yl)-2-(2-tert-butoxycarbonylaminoethoxyimino)acetic acid (syn isomer, 0.40 g.).

Workup

  1. distillationAfter distilling off tetrahydrofuran from the resultant solution
  2. washthe aqueous solution was washed with diethyl ether
  3. extractionThe solution was extracted with ethyl acetate (50 ml.)
  4. washthe extract was washed with a saturated aqueous solution of sodium chloride (10 ml.)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4830eadd58be419f977f29d82f3e6d51
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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