Trifluoroacetic acid → HCID 20190610, compound

HRID 2118842Notes

Reaction equation

HRID 2118842 reaction equation
C(OC([NH:8][CH:9]1[C:12]2([CH2:15][CH2:14][CH2:13]2)[N:11]([O:16][S:17]([OH:20])(=[O:19])=[O:18])[C:10]1=[O:21])=O)(C)(C)C.[Na].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl.C1(C)C=CC=CC=1>[NH2:8][CH:9]1[C:12]2([CH2:15][CH2:14][CH2:13]2)[N:11]([O:16][S:17]([OH:20])(=[O:18])=[O:19])[C:10]1=[O:21]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 5360545SodiumHCID 20190611HCID 20190611, compound

Product 1

HCID 20190610HCID 20190610, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

3-[(t-Butoxycarbonyl)amino]-2-oxo-1-(sulfooxy)-1-azaspiro[3.3]heptane, monosodium salt (0.3 g, 0.87 mmole) was slurried in 2.5 ml of dry dichloromethane and 1.0 ml of anisole at -10° C. under argon, and then treated with 4.0 ml of trifluoroacetic acid. After 0.5 hour, a solid had formed. After 1.5 hours, 4 ml of dry toluene was added, and the mixture evaporated in vacuo to give a solid, 3-amino-2-oxo-1-(sulfooxy)-1-azaspiro[3.3]heptane, which was triturated twice with hexane and dried in vacuo at 25° C. for 1 hour.

Workup

  1. customa solid had formed
  2. waitAfter 1.5 hours
  3. customthe mixture evaporated in vacuo

Sources & evidence

ORD record
ord-cb2009a36af443838b7df86d8ec288a7
Source dataset
uspto-grants-1987_07
Patent number
US04680388

Reaction notes

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