Sodium Sulfate → HCID 53311621, compound

HRID 1401797Notes

Reaction equation

HRID 1401797 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]([CH3:36])([CH3:35])[C:7](=[O:34])[CH2:8][N:9]1[CH2:14][CH2:13][N:12]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:29]=[CH:28][C:27]4[C:26]([CH3:31])([CH3:30])[CH2:25][CH2:24][C:23]([CH3:33])([CH3:32])[C:22]=4[CH:21]=3)[N:19]=2)[CH2:11][CH2:10]1)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:35][C:6]([CH3:36])([CH:7]([OH:34])[CH2:8][N:9]1[CH2:10][CH2:11][N:12]([C:15]2[S:16][CH:17]=[C:18]([C:20]3[CH:29]=[CH:28][C:27]4[C:26]([CH3:31])([CH3:30])[CH2:25][CH2:24][C:23]([CH3:33])([CH3:32])[C:22]=4[CH:21]=3)[N:19]=2)[CH2:13][CH2:14]1)[CH2:5][CH2:4][OH:3]

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 67323323HCID 67323323, compound

Product 1

HCID 53311621HCID 53311621, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

90 mg (0.171 mmol) of 3,3-dimethyl-4-oxo-5-{4-[4-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)thiazol-2-yl]piperazin-1-yl}pentanoic acid ethyl ester from step a was dissolved in 8 ml of THF. 1.71 ml (1.71 mmol) of a 1M lithium aluminium hydride solution in THF was added dropwise with ice-cooling. The mixture was stirred for a further 1 h with cooling, then stirred at room temperature and subsequently at 40° C. overnight, decomposed using a saturated sodium sulfate solution with cooling and extracted twice with EA. The organic phase was washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered, evaporated to dryness and purified by means of preparative HPLC. The product is in the form of the hydrochloride.

Workup

  1. temperaturecooling
  2. temperaturewith cooling
  3. stirringstirred at room temperature and subsequently at 40° C. overnight
  4. temperaturewith cooling
  5. extractionextracted twice with EA
  6. washThe organic phase was washed with a saturated sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. custompurified by means of preparative HPLC

Sources & evidence

ORD record
ord-85f449b815434694bd8dd315cd131de2
Source dataset
uspto-grants-2014_12
Patent number
US08907098B2

Reaction notes

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