Dimethyl Sulfoxide → 9-(4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)nonanal

HRID 1689187Notes

Reaction equation

HRID 1689187 reaction equation
CS(C)=O.C(N(CC)CC)C.[OH:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:22]1[CH2:40][CH2:39][C:25]2([O:30][CH2:29][CH2:28][N:27]([C:31]([C:33]3[N:34]=[C:35]([CH3:38])[S:36][CH:37]=3)=[O:32])[CH2:26]2)[CH2:24][CH2:23]1.S(=O)(=O)=O.N1C=CC=CC=1>ClCCl.[Cl-].[Na+].O>[CH3:38][C:35]1[S:36][CH:37]=[C:33]([C:31]([N:27]2[CH2:26][C:25]3([CH2:39][CH2:40][N:22]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH:13]=[O:12])[CH2:23][CH2:24]3)[O:30][CH2:29][CH2:28]2)=[O:32])[N:34]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 46240299(9-(9-Hydroxynonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone

Product 1

HCID 579892599-(4-(2-Methylthiazole-4-carbonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-9-yl)nonanal

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
-10 °C

Procedure

DMSO (0.32 mL) and triethylamine (0.32 mL) were added to a solution of (9-(9-hydroxynonyl)-1-oxa-4,9-diazaspiro[5.5]undecan-4-yl)(2-methylthiazol-4-yl)methanone (example 2, step a) (0.32 g) in dichloromethane (5 mL). The mixture was cooled in an ice-salt bath and pyridine sulphur trioxide (0.36 g) was added. The reaction was stirred at −10° C. for 1 h then allowed to warm to room temperature and stirred for a further 3 h. The reaction was diluted with DCM (20 mL) then poured into brine (20 mL). The layers were separated and the organic layer washed with brine (20 mL), dried over sodium sulphate, filtered and evaporated in vacuo. Purification was by silica gel chromatography eluting with 47.5:47.5:5 isohexane:ethyl acetate:triethylamine to 95:5 ethyl acetate:triethylamine to gradient to give the subtitled compound as a yellow oil. Yield 0.25 g.

Workup

  1. temperatureThe mixture was cooled in an ice-salt bath
  2. temperatureto warm to room temperature
  3. stirringstirred for a further 3 h
  4. customThe layers were separated
  5. washthe organic layer washed with brine (20 mL)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customPurification
  10. washeluting with 47.5:47.5:5 isohexane

Sources & evidence

ORD record
ord-138487b491ea43ca89f418bffad69f23
Source dataset
uspto-grants-2012_04
Patent number
US08148373B2

Reaction notes

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