Toluene → 3-(3-(2-(8-(2-Isopropylthiazole-4-carbonyl)-5-oxa-2,8-diazaspiro[3.5]nonan-2-yl)ethyl)phenethoxy)propanoic acid trifluoroacetate salt

HRID 1255363Notes

Reaction equation

HRID 1255363 reaction equation
[CH:1]([C:4]1[S:5][CH:6]=[C:7]([C:9]([N:11]2[CH2:39][C:15]3([CH2:18][N:17]([CH2:19][CH2:20][C:21]4[CH:22]=[C:23]([CH:36]=[CH:37][CH:38]=4)[CH2:24][CH2:25][O:26][CH2:27][CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])[CH2:16]3)[O:14][CH2:13][CH2:12]2)=[O:10])[N:8]=1)([CH3:3])[CH3:2].[C:40]([OH:46])([C:42]([F:45])([F:44])[F:43])=[O:41].C1(C)C=CC=CC=1>C(Cl)Cl>[F:43][C:42]([F:45])([F:44])[C:40]([OH:46])=[O:41].[CH:1]([C:4]1[S:5][CH:6]=[C:7]([C:9]([N:11]2[CH2:39][C:15]3([CH2:16][N:17]([CH2:19][CH2:20][C:21]4[CH:22]=[C:23]([CH:36]=[CH:37][CH:38]=4)[CH2:24][CH2:25][O:26][CH2:27][CH2:28][C:29]([OH:31])=[O:30])[CH2:18]3)[O:14][CH2:13][CH2:12]2)=[O:10])[N:8]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6422Trifluoroacetic acidHCID 58168616tert-Butyl 3-(3-(2-(8-(2-isopropylthiazole-4-carbonyl)-5-oxa-2,8-diazaspiro[3.5]nonan-2-yl)ethyl)phenethoxy)propanoate

Product 1

HCID 669637513-(3-(2-(8-(2-Isopropylthiazole-4-carbonyl)-5-oxa-2,8-diazaspiro[3.5]nonan-2-yl)ethyl)phenethoxy)propanoic acid trifluoroacetate salt

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 3-(3-(2-(8-(2-isopropylthiazole-4-carbonyl)-5-oxa-2,8-diazaspiro[3.5]nonan-2-yl)ethyl)phenethoxy)propanoate (460 mg) (example 176 step g) in DCM (6 mL) was treated with TFA (2 mL) and the solution allowed to stand at RT for 1 hour. Toluene (10 mL) was added and the solvents were evaporated under reduced pressure and the residue dissolved in acetonitrile and the solution evaporated under reduced pressure to afford the subtitled compound. Yield 500 mg.

Workup

  1. customthe solvents were evaporated under reduced pressure
  2. dissolutionthe residue dissolved in acetonitrile
  3. customthe solution evaporated under reduced pressure

Sources & evidence

ORD record
ord-76e8fce5995b48348a270ad78014df27
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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