Toluene → (2,2-Difluoro-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone trifluoroacetate

HRID 1689306Notes

Reaction equation

HRID 1689306 reaction equation
C(OC([N:8]1[CH2:30][CH2:29][C:11]2([O:16][C:15]([F:18])([F:17])[CH2:14][N:13]([C:19]([C:21]3[N:22]=[C:23]([CH:26]([CH3:28])[CH3:27])[S:24][CH:25]=3)=[O:20])[CH2:12]2)[CH2:10][CH2:9]1)=O)(C)(C)C.[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].C1(C)C=CC=CC=1>C(Cl)Cl>[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[F:18][C:15]1([F:17])[CH2:14][N:13]([C:19]([C:21]2[N:22]=[C:23]([CH:26]([CH3:28])[CH3:27])[S:24][CH:25]=2)=[O:20])[CH2:12][C:11]2([CH2:29][CH2:30][NH:8][CH2:9][CH2:10]2)[O:16]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57989035Tert-butyl-2,2-difluoro-4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 67292751(2,2-Difluoro-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-isopropylthiazol-4-yl)methanone trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl-2,2-difluoro-4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (example 44, step a) (0.78 g) in DCM (20 mL) was treated with trifluoroacetic acid (5 mL) and the reaction mixture allowed to stand at 20° C. for 30 minutes. Toluene (40 mL) was added and the solvents evaporated under reduced pressure. The residue was azeotroped twice with acetonitrile to afford the subtitled compound. Yield 0.8 g.

Workup

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

Sources & evidence

ORD record
ord-38ebc8364d794d11a2f760875f948a18
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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