Potassium Sodium Tartrate → HCID 59201637, compound

HRID 451879Notes

Reaction equation

HRID 451879 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C@@H:7]([CH2:23][O:24][S:25]([C:28]1[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=1)(=[O:27])=[O:26])[CH2:8][C@H:9]1[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[N:10]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])C.[CH3:36][CH2:37][Mg+].[Br-].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1.CCOC(C)=O>[OH:3][C:4]1([CH2:5][CH2:6][C@@H:7]([CH2:23][O:24][S:25]([C:28]2[CH:34]=[CH:33][C:31]([CH3:32])=[CH:30][CH:29]=2)(=[O:26])=[O:27])[CH2:8][C@H:9]2[CH2:13][O:12][C:11]([CH3:14])([CH3:15])[N:10]2[C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])[CH2:37][CH2:36]1

Participants

6

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 59201710HCID 59201710, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 59201637HCID 59201637, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(S)-tert-Butyl 4-((R)-5-ethoxy-5-oxo-2-(tosyloxymethyl)pentyl)-2,2-dimethyloxazolidine-3-carboxylate (1.82 g, 3.55 mmol) and Ti(Oi-Pr)4 were dissolved in THF (30 mL) and allowed to stir at ambient temperature. A solution of EtMgBr (3.0 M, 5.91 mL, 17.8 mmol, 5.0 equiv) was added over a 6 hr period via syringe pump and the resulting mixture stirred overnight. The mixture was treated with a 50% solution of Rochelle's salt and diluted with EtOAc. The layers were separated and the aqueous layer extracted with additional EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered and evaporated. The resulting crude (S)-tert-butyl 4-((R)-4-(1-hydroxycyclopropyl)-2-(tosyloxymethyl)butyl)-2,2-dimethyloxazolidine-3-carboxylate was used in the next step with no further purification.

Workup

  1. stirringthe resulting mixture stirred overnight
  2. customThe layers were separated
  3. extractionthe aqueous layer extracted with additional EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting crude (S)-tert-butyl 4-((R)-4-(1-hydroxycyclopropyl)-2-(tosyloxymethyl)butyl)-2,2-dimethyloxazolidine-3-carboxylate was used in the next step with no further purification

Sources & evidence

ORD record
ord-b6ce46aaa5a344be8ad011fe48810873
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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