Trifluoroacetic acid → HCID 67165365, compound

HRID 552350Notes

Reaction equation

HRID 552350 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([N:15]1[C:19]2([CH2:24][CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21][CH2:20]2)[NH:18][C@@H:17]([CH2:32][C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:16]1=[O:39])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:8]([N:15]1[C:19]2([CH2:20][CH2:21][NH:22][CH2:23][CH2:24]2)[NH:18][C@@H:17]([CH2:32][C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:16]1=[O:39])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 67166125HCID 67166125, compound

Product 1

HCID 67165365HCID 67165365, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (68.5 g, 601 mmol) was added dropwise at 0° C. to a solution of tert-butyl 1,3-(S)-dibenzyl-2-oxo-1,4,8-triazaspiro[4,5]decane-8-carboxylate (13.5 g, 31.0 mmol) in CH2Cl2 (93 ml) and the mixture was stirred at this temperature for 15 min. After warming to RT, the reaction mixture was stirred for a further 2.5 h. Subsequently, the reaction solution was adjusted with aqueous saturated NaHCO3 solution to pH 7-8, the organic phase was separated off and the aqueous phase was extracted with CH2Cl2 (2×30 ml). The combined organic phase was dried over Na2SO4, filtered and the solvent was distilled off. The workup was carried out by means of column chromatography and afforded 1,3-(S)-dibenzyl-1,4,8-triazaspiro[4,5]decan-2-one in a yield of 7.8 g (75%).

Workup

  1. stirringthe reaction mixture was stirred for a further 2.5 h
  2. customthe organic phase was separated off
  3. extractionthe aqueous phase was extracted with CH2Cl2 (2×30 ml)
  4. dry with materialThe combined organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-c2c8f9b7346b4674a01f5ed40f41a5d0
Source dataset
uspto-grants-2011_05
Patent number
US07951815B2

Reaction notes

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