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

HRID 1689496Notes

Reaction equation

HRID 1689496 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-4d5216e1a6634a82968b3809033ab5b1
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

Loading…