Acetic Acid → 2-(Formylamino)methyl-4-methoxycarbonylaminothiazole

HRID 1603468Notes

Reaction equation

HRID 1603468 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13]([NH:15][CH2:16][C:17]1[S:18][CH:19]=[C:20]([NH:22][C:23]([O:25][CH3:26])=[O:24])[N:21]=1)=O)(C)(C)C.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)C>ClCCl.C(O)=O>[CH:13]([NH:15][CH2:16][C:17]1[S:18][CH:19]=[C:20]([NH:22][C:23]([O:25][CH3:26])=[O:24])[N:21]=1)=[O:12]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 196051602-(N-t-butoxycarbonylamino)methyl-4-methoxycarbonylaminothiazole

Product 1

HCID 196050292-(Formylamino)methyl-4-methoxycarbonylaminothiazoleYield 100%

Reagents, catalysts & solvents 2

HCID 284Formic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

A 3.9 ml portion of trifluoroacetic acid was added to 776 mg of 2-(N-t-butoxycarbonylamino)methyl-4-methoxycarbonylaminothiazole, followed by stirring at room temperature for 50 minutes. The reagent was evaporated under reduced pressure to obtain a light brown solid, and this solid was then dissolved in 13.5 ml of dichloromethane and 10 ml of a 15% aqueous potassium carbonate solution to adjust the pH of the solution to 10.0. Further, a mixed solution of 2.55 ml of anhydrous acetic acid and 1.27 ml of formic acid was added dropwise over 10 minutes under ice-cooling with vigorous stirring. After adjustment to pH 6 with potassium carbonate, the ice bath was removed, and the solution was then stirred for 30 minutes. After the addition of 100 ml of dichloromethane and 20 ml of distilled water as well as sufficient shaking, the organic layer was separated. After the pH of the aqueous layer was adjusted to 11 with potassium carbonate, extraction was carried out twice with 100 ml of dichloromethane, and the extract was then combined with the above organic layer. Further, the solution was dried (anhydrous magnesium sulfate and anhydrous potassium carbonate), and then filtered. The solvent was then evaporated under reduced pressure to obtain 581 mg of 2-(formylamino)methyl-4-methoxycarbonylaminothiazole as a light yellow powder.

Workup

  1. customThe reagent was evaporated under reduced pressure
  2. customto obtain a light brown solid
  3. temperaturecooling with vigorous stirring
  4. customAfter adjustment to pH 6 with potassium carbonate, the ice bath was removed
  5. stirringthe solution was then stirred for 30 minutes
  6. additionAfter the addition of 100 ml of dichloromethane and 20 ml of distilled water as well as sufficient shaking
  7. customthe organic layer was separated
  8. extractionAfter the pH of the aqueous layer was adjusted to 11 with potassium carbonate, extraction
  9. dry with materialFurther, the solution was dried (anhydrous magnesium sulfate and anhydrous potassium carbonate)
  10. filtrationfiltered
  11. customThe solvent was then evaporated under reduced pressure

Sources & evidence

ORD record
ord-e54df7eeb3dd42d5b6213bdd6a66f31f
Source dataset
uspto-grants-1999_11
Patent number
US05990101

Reaction notes

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