Trifluoroacetic acid → (2-Isopropylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate

HRID 471088Notes

Reaction equation

HRID 471088 reaction equation
[CH:1]([C:4]1[S:5][CH:6]=[C:7]([C:9]([N:11]2[CH2:16][C:15]3([CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[O:14][CH2:13][CH2:12]2)=[O:10])[N:8]=1)([CH3:3])[CH3:2].[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32]>C(Cl)Cl>[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32].[CH:1]([C:4]1[S:5][CH:6]=[C:7]([C:9]([N:11]2[CH2:16][C:15]3([CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)[O:14][CH2:13][CH2:12]2)=[O:10])[N:8]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57989200tert-Butyl 4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 66964182(2-Isopropylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (limiting reagent) (step a) in DCM (5 volumes) was added trifluoroacetic acid (13.4 molar equivalents) in portions at 10-15° C. The solution was allowed to warm to ambient and stirred for 16 hr. Solvent was evaporated and the residue was dissolved in diethyl ether (10 volumes). The solution was cooled in ice and scratched to give precipitation; the slurry was stirred at 0°-10° C. for 0.5 hr then filtered cold. The cake was washed with diethyl ether (5 volumes) and dried in vacuo at 35° C. to give a beige coloured powder. Yield: 91% of theoretical.

Workup

  1. temperatureto warm to ambient and
  2. customSolvent was evaporated
  3. dissolutionthe residue was dissolved in diethyl ether (10 volumes)
  4. temperatureThe solution was cooled in ice
  5. customto give
  6. customprecipitation
  7. stirringthe slurry was stirred at 0°-10° C. for 0.5 hr
  8. filtrationthen filtered cold
  9. washThe cake was washed with diethyl ether (5 volumes)
  10. customdried in vacuo at 35° C.
  11. customto give

Sources & evidence

ORD record
ord-0ec1c7b59dcb494285fc3299a4ab5b83
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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