Hydrochloric Acid → HCID 12893157, compound

HRID 1381379Notes

Reaction equation

HRID 1381379 reaction equation
C([O:3][C:4](=[O:13])[CH:5]([C:7]1[N:8]=[C:9]([NH2:12])[S:10][CH:11]=1)[NH2:6])C.[OH-].[Na+].Cl.[C:17]([O:21][C:22](ON=C(C1C=CC=CC=1)C#N)=[O:23])([CH3:20])([CH3:19])[CH3:18]>CO.C(N(CC)CC)C.O>[C:17]([O:21][C:22]([NH:6][CH:5]([C:7]1[N:8]=[C:9]([NH2:12])[S:10][CH:11]=1)[C:4]([OH:3])=[O:13])=[O:23])([CH3:20])([CH3:19])[CH3:18]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 938652-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrileHCID 15137543HCID 15137543, compound

Product 1

HCID 12893157HCID 12893157, compoundYield 31.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 2-(2-aminothiazol-4-yl)glycine ethyl ester (24.2 g) and 2N aqueous solution of sodium hydroxide (7.2 g) in methanol (240 ml) was stirred at ambient temperature for an hour. After adjusting to pH 7 with conc. hydrochloric acid, water (250 ml), and then 2-tert-butoxycarbonyloxyimino-2-phenylacetonitrile (29.5 g) and triethylamine (18.2 g) were added thereto. After stirring at ambient temperature for an hour, the reaction mixture was evaporated. The resultant aqueous solution was washed twice with ethyl acetate, followed by adding ethyl acetate and adjusting to pH 7 with 10% hydrochloric acid. After removal of the insoluble substance by filtration, the aqueous layer was separated out, adjusted to pH 4 with 10% hydrochloric acid and treated with activated charcoal. To the filtrate was added sodium chloride, followed by stirring under ice-cooling. The precipitated solid was collected by filtration and dried to give N-tert-butoxycarbonyl-2-(2-aminothiazol-4-yl)glycine (10.2 g).

Workup

  1. stirringAfter stirring at ambient temperature for an hour
  2. customthe reaction mixture was evaporated
  3. washThe resultant aqueous solution was washed twice with ethyl acetate
  4. additionby adding ethyl acetate
  5. customAfter removal of the insoluble substance
  6. filtrationby filtration
  7. customthe aqueous layer was separated out
  8. additiontreated with activated charcoal
  9. additionTo the filtrate was added sodium chloride
  10. stirringby stirring under ice-
  11. temperaturecooling
  12. filtrationThe precipitated solid was collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-7eeaa43dfe8a4601be8b35ffc09ae4b0
Source dataset
uspto-grants-1986_04
Patent number
US04585860

Reaction notes

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