Toluene → (2-Phenylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

HRID 1689492

Reaction equation

HRID 1689492 reaction equation
FC(F)(F)C(O)=O.[C:8]1([C:14]2[S:15][CH:16]=[C:17]([C:19]([N:21]3[CH2:26][C:25]4([CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27]4)[O:24][CH2:23][CH2:22]3)=[O:20])[N:18]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C1(C)C=CC=CC=1>C(Cl)Cl>[C:8]1([C:14]2[S:15][CH:16]=[C:17]([C:19]([N:21]3[CH2:26][C:25]4([CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[O:24][CH2:23][CH2:22]3)=[O:20])[N:18]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57989358tert-Butyl 4-(2-phenylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 57989130(2-Phenylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3.8 mL) was added to a solution of tert-butyl 4-(2-phenylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (example 112, step a) (0.85 mg) in DCM (15.2 mL). The resulting mixture was stirred at RT for 1 h. Toluene (30 mL) was added and the mixture was evaporated in vacuo. The yellow residue was dissolved in MeOH and applied to a SCX cartridge pre-wetted with MeOH. The cartridge was washed with MeOH and eluted with 2M ammonia in MeOH. The eluent was evaporated in vacuo to give the subtitled compound as a brown oil. Yield 0.629 g.

Workup

  1. customthe mixture was evaporated in vacuo
  2. dissolutionThe yellow residue was dissolved in MeOH
  3. washThe cartridge was washed with MeOH
  4. washeluted with 2M ammonia in MeOH
  5. customThe eluent was evaporated in vacuo

Sources & evidence

ORD record
ord-0fa817b721e947c4b44ac1e15c6c7944
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Linked notes

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