Toluene → (2-Isopropylthiazol-5-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

HRID 471266Notes

Reaction equation

HRID 471266 reaction equation
FC(F)(F)C(O)=O.[CH:8]([C:11]1[S:12][C:13]([C:16]([N:18]2[CH2:23][C:22]3([CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]3)[O:21][CH2:20][CH2:19]2)=[O:17])=[CH:14][N:15]=1)([CH3:10])[CH3:9].C1(C)C=CC=CC=1>C(Cl)Cl>[CH:8]([C:11]1[S:12][C:13]([C:16]([N:18]2[CH2:23][C:22]3([CH2:24][CH2:25][NH:26][CH2:27][CH2:28]3)[O:21][CH2:20][CH2:19]2)=[O:17])=[CH:14][N:15]=1)([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57989386tert-Butyl 4-(2-isopropylthiazole-5-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 57989156(2-Isopropylthiazol-5-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (3.9 mL) was added to a solution of tert-butyl 4-(2-isopropylthiazole-5-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (example 113, step a) (0.765 g) in DCM (14.8 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 yellow oil. Yield 0.552 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-62e82f9cfcf64377bdc78e1cdcc6c795
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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