Trifluoroacetic acid → (2-Ethylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate

HRID 446436Notes

Reaction equation

HRID 446436 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([C:10]1[S:11][CH:12]=[C:13]([C:15]([N:17]2[CH2:22][C:21]3([CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)[O:20][CH2:19][CH2:18]2)=[O:16])[N:14]=1)[CH3:9]>ClCCl.C1(C)C=CC=CC=1>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([C:10]1[S:11][CH:12]=[C:13]([C:15]([N:17]2[CH2:22][C:21]3([CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[O:20][CH2:19][CH2:18]2)=[O:16])[N:14]=1)[CH3:9]

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58168458Tert-butyl 4-(2-ethylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 66964094(2-Ethylthiazol-4-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone trifluoroacetate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (20 mL) was added to a solution of tert-butyl 4-(2-ethylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate [Example 26, step a] (24 g) in dichloromethane (100 mL) and the mixture stirred at ambient temperature for 18 hours. The reaction mixture was diluted with toluene (50 mL) and concentrated in vacuo. The residue was dissolved in dichloromethane (50 mL), TFA (50 mL) was added and the mixture was stirred for 4 hours. The mixture was diluted with toluene (50 mL), concentrated in vacuo, the residue triturated with ether and the precipitated solid collected by filtration and dried to afford the subtitled compound as a white solid. Yield 28 g.

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in dichloromethane (50 mL)
  3. additionTFA (50 mL) was added
  4. stirringthe mixture was stirred for 4 hours
  5. additionThe mixture was diluted with toluene (50 mL)
  6. concentrationconcentrated in vacuo
  7. customthe residue triturated with ether
  8. filtrationthe precipitated solid collected by filtration
  9. customdried

Sources & evidence

ORD record
ord-549c6826e3534c21946ae1c79e0d672c
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

Loading…