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

HRID 1689442Notes

Reaction equation

HRID 1689442 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-bc26712943da42b987af572a3ef0c2f6
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

Loading…