Toluene → (2-Methylthiazol-4-yl)(7-oxa-3,10-diazaspiro[5.6]dodecan-10-yl)methanone trifluoroacetate

HRID 471212Notes

Reaction equation

HRID 471212 reaction equation
[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([N:9]2[CH2:27][CH2:26][C:13]3([CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]3)[O:12][CH2:11][CH2:10]2)=[O:8])[N:6]=1.[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31].C1(C)C=CC=CC=1>C(Cl)Cl>[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31].[CH3:1][C:2]1[S:3][CH:4]=[C:5]([C:7]([N:9]2[CH2:27][CH2:26][C:13]3([CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)[O:12][CH2:11][CH2:10]2)=[O:8])[N:6]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57989321tert-Butyl 10-(2-methylthiazole-4-carbonyl)-7-oxa-3,10-diazaspiro[5.6]dodecane-3-carboxylate

Product 1

HCID 67292347(2-Methylthiazol-4-yl)(7-oxa-3,10-diazaspiro[5.6]dodecan-10-yl)methanone trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 10-(2-methylthiazole-4-carbonyl)-7-oxa-3,10-diazaspiro[5.6]dodecane-3-carboxylate (example 89, step f) (0.21 g) in DCM (10 mL) was treated with trifluoroacetic acid (10 mL) and the solution allowed to stand at 20° C. for 25 minutes. Toluene (40 mL) was added and the solvents evaporated under reduced pressure. The residue was azeotroped with acetonitrile to afford the subtitled compound. Yield 0.21 g.

Workup

  1. customthe solvents evaporated under reduced pressure
  2. customThe residue was azeotroped with acetonitrile

Sources & evidence

ORD record
ord-29b61c011b6a4d3dad05f4d567fa49bd
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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