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 446464Notes

Reaction equation

HRID 446464 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-73f46f94d2d0411094377d39ea6edd6e
Source dataset
uspto-grants-2013_07
Patent number
US08476265B2

Reaction notes

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