Lithium hydroxide, monohydrate → HCID 125496396, compound

HRID 1478194Notes

Reaction equation

HRID 1478194 reaction equation
O.[OH-].[Li+].[Si:4]([O:11][C@@H:12]([CH3:30])[C@H:13]([C:19]1[O:23][N:22]=[C:21]([C:24]([O:26]CC)=[O:25])[C:20]=1[CH3:29])[O:14][CH2:15][C:16]([CH3:18])=[CH2:17])([C:7]([CH3:10])([CH3:9])[CH3:8])([CH3:6])[CH3:5].[Si](O[C@@H](C)[C@H](C1ON=C(C(OCC(C)=C)=O)C=1C)OCC(C)=C)(C(C)(C)C)(C)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.O>[Si:4]([O:11][C@@H:12]([CH3:30])[C@H:13]([C:19]1[O:23][N:22]=[C:21]([C:24]([OH:26])=[O:25])[C:20]=1[CH3:29])[O:14][CH2:15][C:16]([CH3:18])=[CH2:17])([C:7]([CH3:10])([CH3:8])[CH3:9])([CH3:5])[CH3:6]

Participants

6

Reactant 3

HCID 168937Lithium hydroxide, monohydrateHCID 131736502HCID 131736502, compoundHCID 131736503HCID 131736503, compound

Product 1

HCID 125496396HCID 125496396, compound

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
70 °C

Procedure

Lithium Hydroxide monohydrate (3.20 g, 76 mmol) was added portionwise to a mixture of ethyl 5-((1R,2S)-2-((tert-butyldimethyl silyl)oxy)-1-((2-methylallyl)oxy)propyl)-4-methylisoxazole-3-carboxylate and 2-methylallyl 5-((1R,2S)-2-((tert-butyldimethylsilyl)oxy)-1-((2-methylallyl)oxy)propyl)-4-methylisoxazole-3-carboxylate [4.5 g as an approximate 9:1 mixture containing residual Tetrabutyl ammonium iodide (25% w/w)] in THF/water (300 mL, 1.5/1.0) and the resulting mixture was heated gently at 70° C. After cooling to room temperature the layers were separated and the remaining aqueous was acidified with 1 M aqueous hydrochloric acid and extracted with EtOAc. The organic extracts were combined and washed with brine, dried over Na2SO4 and concentrated under reduced pressure to afford the crude title compound;

Workup

  1. temperatureAfter cooling to room temperature the layers
  2. customwere separated
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1e0b41dfb79443fb8cf40f35c4f7e799
Source dataset
uspto-grants-2016_08
Patent number
US09403810B2

Reaction notes

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