Toluene → 3-(4-(2-(4-(2-Isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanoic acid

HRID 1255301Notes

Reaction equation

HRID 1255301 reaction equation
FC(F)(F)C(O)=O.[CH:8]([C:11]1[S:12][CH:13]=[C:14]([C:16]([N:18]2[CH2:23][C:22]3([CH2:28][CH2:27][N:26]([CH2:29][CH2:30][C:31]4[CH:48]=[CH:47][C:34]([CH2:35][CH2:36][O:37][CH2:38][CH2:39][C:40]([O:42]C(C)(C)C)=[O:41])=[CH:33][CH:32]=4)[CH2:25][CH2:24]3)[O:21][CH2:20][CH2:19]2)=[O:17])[N:15]=1)([CH3:10])[CH3:9].C1(C)C=CC=CC=1>C(Cl)Cl>[CH:8]([C:11]1[S:12][CH:13]=[C:14]([C:16]([N:18]2[CH2:23][C:22]3([CH2:24][CH2:25][N:26]([CH2:29][CH2:30][C:31]4[CH:32]=[CH:33][C:34]([CH2:35][CH2:36][O:37][CH2:38][CH2:39][C:40]([OH:42])=[O:41])=[CH:47][CH:48]=4)[CH2:27][CH2:28]3)[O:21][CH2:20][CH2:19]2)=[O:17])[N:15]=1)([CH3:10])[CH3:9]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 58168551tert-Butyl 3-(4-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanoate

Product 1

HCID 462387963-(4-(2-(4-(2-Isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (10 mL) was added to a solution of tert-butyl 3-(4-(2-(4-(2-isopropylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)ethyl)phenethoxy)propanoate [Example 1, step d] (0.55 g) in DCM (20 mL) and the resultant solution allowed to stand at 20° C. for 1 hour. Toluene (30 mL) was added and the solvents were evaporated under reduced pressure. The residue was azeotroped with acetonitrile (×2) to yield the subtitled compound. Yield 0.60 g.

Workup

  1. customthe solvents were evaporated under reduced pressure
  2. customThe residue was azeotroped with acetonitrile (×2)

Sources & evidence

ORD record
ord-4b6a30b87eb84db186965153769ba8c3
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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