Trifluoroacetic acid → HCID 13754464, compound

HRID 980576Notes

Reaction equation

HRID 980576 reaction equation
C(OC([NH:8][CH:9]1[C:12]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[N:11]([O:17][S:18]([OH:21])(=[O:20])=[O:19])[C:10]1=[O:22])=O)(C)(C)C.[K].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[NH2:8][CH:9]1[C:12]2([CH2:16][CH2:15][CH2:14][CH2:13]2)[N:11]([O:17][S:18]([OH:21])(=[O:19])=[O:20])[C:10]1=[O:22]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 5462222PotassiumHCID 13754463HCID 13754463, compound

Product 1

HCID 13754464HCID 13754464, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

3[(t-Butoxycarbonyl)amino]-2-oxo-1-(sulfooxy)-1-azaspiro[3.4]octane, monopotassium salt (280 mg, 0.75 mmoles) was covered with 2 ml of dry dichloromethane, 0.8 ml of anisole was added, and the mixture cooled to -10° C. Trifluoroacetic acid (3 ml) was added, and the solution was stirred at -10 to -5° C. for 1.5 hours. After 0.75 hours a solid formed, becoming quite substantial by 1.5 hours. The volatiles were evaporated in vacuo and the solid residue triturated with ether to give 3-amino-2-oxo-1-(sulfooxy)-1-azaspiro[3.4]octane.

Workup

  1. additionwas added
  2. customAfter 0.75 hours a solid formed
  3. waitbecoming quite substantial by 1.5 hours
  4. customThe volatiles were evaporated in vacuo
  5. customthe solid residue triturated with ether

Sources & evidence

ORD record
ord-75ed9fb20a0143478f577dcb6139f5ad
Source dataset
uspto-grants-1987_01
Patent number
US04638060

Reaction notes

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