HCID 20226079, compound → HCID 20226076, compound

HRID 1248817Notes

Reaction equation

HRID 1248817 reaction equation
C(OC([NH:8][C:9]1[S:13][N:12]=[C:11](/[C:14](/[C:17]([OH:19])=[O:18])=[CH:15]/[CH3:16])[N:10]=1)=O)(C)(C)C>FC(F)(F)C(O)=O>[NH2:8][C:9]1[S:13][N:12]=[C:11](/[C:14](/[C:17]([OH:19])=[O:18])=[CH:15]/[CH3:16])[N:10]=1

Participants

3

Reactant 1

HCID 20226079HCID 20226079, compound

Product 1

HCID 20226076HCID 20226076, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

340 mg (1.2 mMol) of Z-1-(5-t-butoxycarbonylamino-1,2,4-thiadiazol-3-yl)propene-1-carboxylic acid were dissolved in 4 ml of trifluoroacetic acid at 0° C. and stirred at 0° C. for 2 hours. The trifluoroacetic acid was now removed in vacuo, and the residue was dissolved 2×in CH2Cl2 which was again removed in vacuo each time. The residue was dissolved in 5 ml of water, the pH was adjusted to 4 with 1N NaOH, and the mixture was extracted 3×20 ml of ethyl acetate, which was discarded. The evaporated aqueous phase was filtered through 25 g of silica gel using CHCl3 /CH3OH (3:1) and the solvent was evaporated.

Workup

  1. customThe trifluoroacetic acid was now removed in vacuo
  2. dissolutionthe residue was dissolved 2×in CH2Cl2 which
  3. customwas again removed in vacuo each time
  4. dissolutionThe residue was dissolved in 5 ml of water
  5. extractionthe mixture was extracted 3×20 ml of ethyl acetate, which
  6. filtrationThe evaporated aqueous phase was filtered through 25 g of silica gel
  7. customthe solvent was evaporated

Sources & evidence

ORD record
ord-681b672247c34dd4a6434b3bf1646558
Source dataset
uspto-grants-1986_12
Patent number
US04626535

Reaction notes

Loading…