Sodium Bicarbonate → 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 1255344Notes

Reaction equation

HRID 1255344 reaction equation
[CH:1]1([N:7]([CH2:41][CH:42](OC)[O:43]C)[C:8](=[O:40])[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]3[CH2:39][CH2:38][C:24]4([O:29][CH2:28][CH2:27][N:26]([C:30]([C:32]5[N:33]=[C:34]([CH3:37])[S:35][CH:36]=5)=[O:31])[CH2:25]4)[CH2:23][CH2:22]3)[CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH:1]1([N:7]([CH2:41][CH:42]=[O:43])[C:8](=[O:40])[CH2:9][CH2:10][O:11][CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][N:21]3[CH2:39][CH2:38][C:24]4([O:29][CH2:28][CH2:27][N:26]([C:30]([C:32]5[N:33]=[C:34]([CH3:37])[S:35][CH:36]=5)=[O:31])[CH2:25]4)[CH2:23][CH2:22]3)[CH:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 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 monohydrate (1.38 g) 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 (0.68 g) in DCM (10 mL) and the resulting mixture stirred at RT until consumption of the acetal was complete (4 h). Saturated sodium bicarbonate solution (10 mL) was cautiously added and the mixture was stirred until bubbling ceased (10 min). The reaction mixture was diluted with DCM (50 mL) and the aqueous phase separated. The organic phase was washed with saturated sodium bicarbonate solution (2×20 mL) and brine (20 mL), dried over sodium sulphate, filtered and evaporated to give the subtitled compound as a gum. Yield 0.61 g.

Workup

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

Sources & evidence

ORD record
ord-7d2b022a92d14a3dae8cd3b00a6f8e56
Source dataset
uspto-grants-2013_06
Patent number
US08455483B2

Reaction notes

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