Hydrochloric Acid → HCID 59730426, compound

HRID 130318Notes

Reaction equation

HRID 130318 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[CH:9]=[C:10]([C@:14]2([CH3:30])[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[O:21])[CH2:16][C@@H:15]2[CH3:29])[CH:11]=[CH:12][CH:13]=1)=[O:7].Cl>O.O1CCCC1>[C:6]([C:8]1[CH:9]=[C:10]([C@:14]2([CH3:30])[CH2:19][CH2:18][N:17]([C:20]([O:22][CH2:23][CH2:24][Si:25]([CH3:28])([CH3:27])[CH3:26])=[O:21])[CH2:16][C@@H:15]2[CH3:29])[CH:11]=[CH:12][CH:13]=1)([OH:7])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 59730457HCID 59730457, compound

Product 1

HCID 59730426HCID 59730426, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (2.75 g, 0.065 mol, 6 eq) in water (20 mL) was added drop wise to a cold (0° C.) solution of (6) (4.28 g, 0.0109 mol, 1 eq) in tetrahydrofuran (40 mL). The mixture was allowed to warm to room temperature and stirring was continued for 5 days. A 1N aqueous HCl solution (100 mL) was added to the mixture which was extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with water (100 mL), brine (100 mL) and dried over sodium sulfate. Evaporation of the solvent afforded the desired compound (4.0 g, 97%).

Workup

  1. extractionwas extracted with ethyl acetate (3×100 mL)
  2. washThe combined organic extracts were washed with water (100 mL), brine (100 mL)
  3. dry with materialdried over sodium sulfate
  4. customEvaporation of the solvent

Sources & evidence

ORD record
ord-60f75797ad4a4f1aa8db488a9c8cb849
Source dataset
uspto-grants-2008_06
Patent number
US07381721B2

Reaction notes

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