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

HRID 1689368Notes

Reaction equation

HRID 1689368 reaction equation
[CH:1]([C:4]1[N:5]=[C:6]([C:9]([N:11]2[CH2:16][C:15]3([CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]3)[O:14][CH2:13][CH2:12]2)=[O:10])[S:7][CH:8]=1)([CH3:3])[CH3:2].FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>C(Cl)Cl>[CH:1]([C:4]1[N:5]=[C:6]([C:9]([N:11]2[CH2:16][C:15]3([CH2:17][CH2:18][NH:19][CH2:20][CH2:21]3)[O:14][CH2:13][CH2:12]2)=[O:10])[S:7][CH:8]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 57988958tert-Butyl 4-(4-isopropylthiazole-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate

Product 1

HCID 57989334(4-Isopropylthiazol-2-yl)(1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-(4-isopropylthiazole-2-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecane-9-carboxylate (example 66, step a) (0.54 g) in DCM (20 mL) was treated with trifluoroacetic acid (5 mL) and the reaction mixture allowed to stand at 20° C. for 20 minutes. Toluene (40 mL) was added and the solvents removed under reduced pressure. The residue was azeotroped twice with acetonitrile to afford the subtitled compound. Yield 0.56 g.

Workup

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

Sources & evidence

ORD record
ord-bcaeb91742a348e88d519e300996cd6f
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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