p-Toluenesulfonic acid → N-Cyclohexyl-3-(3-((4-(2-methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)-N-(2-oxoethyl)propanamide

HRID 471302Notes

Reaction equation

HRID 471302 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.[CH:12]1([N:18]([CH2:52][CH:53](OC)[O:54]C)[C:19](=[O:51])[CH2:20][CH2:21][O:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][N:32]3[CH2:50][CH2:49][C:35]4([O:40][CH2:39][CH2:38][N:37]([C:41]([C:43]5[N:44]=[C:45]([CH3:48])[S:46][CH:47]=5)=[O:42])[CH2:36]4)[CH2:34][CH2:33]3)[CH:26]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:12]1([N:18]([CH2:52][CH:53]=[O:54])[C:19](=[O:51])[CH2:20][CH2:21][O:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31][N:32]3[CH2:50][CH2:49][C:35]4([O:40][CH2:39][CH2:38][N:37]([C:41]([C:43]5[N:44]=[C:45]([CH3:48])[S:46][CH:47]=5)=[O:42])[CH2:36]4)[CH2:34][CH2:33]3)[CH:26]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 57989141N-Cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-((4-(2-methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanamide

Product 1

HCID 57989266N-Cyclohexyl-3-(3-((4-(2-methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)-N-(2-oxoethyl)propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Tosic acid (1384 mg) was added to a solution of N-cyclohexyl-N-(2,2-dimethoxyethyl)-3-(3-((4-(2-methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)methyl)phenethoxy)propanamide (Example 277, step c) (683 mg) in DCM (10 mL) and the resulting mixture stirred at ambient temperature for 4 h. Sodium bicarbonate solution (saturated, 10 mL) was cautiously added and the mixture stirred until bubbling ceased (10 min). The reaction was diluted with DCM (50 mL) and the aqeuous separated. The organic was washed with saturated sodium bicarbonate solution (2×20 mL), brine (20 mL), dried over sodium sulphate, filtered and evaporated to afford the subtitled compound.

Workup

  1. stirringthe mixture stirred
  2. customuntil bubbling
  3. custom(10 min)
  4. additionThe reaction was diluted with DCM (50 mL)
  5. washThe organic was washed with saturated sodium bicarbonate solution (2×20 mL), brine (20 mL)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-8dd43bd1a5c64c07b03d77c69f9580d0
Source dataset
uspto-grants-2014_01
Patent number
US08629271B2

Reaction notes

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