Hydrochloric Acid → HCID 18468579, compound

HRID 2229524Notes

Reaction equation

HRID 2229524 reaction equation
C([Li])CCC.C(NC(C)C)(C)C.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([NH:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])=[O:21])=[CH:16][CH:15]=1.[CH2:29]([O:36][CH2:37]Cl)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Cl>CCCCCC.O1CCCC1.CN(C)P(N(C)C)(N(C)C)=O>[CH2:29]([O:36][CH2:37][CH:25]([CH2:24][CH2:23][NH:22][C:20]([C:17]1[CH:18]=[CH:19][C:14]([CH3:13])=[CH:15][CH:16]=1)=[O:21])[C:26]([OH:28])=[O:27])[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 137983Benzyl chloromethyl etherHCID 16769036HCID 16769036, compoundHCID 178418339Butyllithium

Product 1

HCID 18468579HCID 18468579, compoundYield 32.3%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
-78 °C

Procedure

Under an atmosphere of argon, 1.63M n-butyl lithium in hexane (4.05 ml) was added to a solution of diisopropylamine (0.925 ml) in tetrahydrofuran (5 ml) and hexamethyl phosphoramide (HMPA) (3 ml) at −78° C. The mixture was stirred at −78° C. for 15 minutes. A solution of the compound prepared in Example 2(1) (0.442 g) in tetrahydrofuran (3 ml) was added to this solution at −78° C. The mixture was stirred at room temperature for 30 minutes. Benzyloxymethyl chloride (0.313 g) was added to the reaction mixture at −78° C. The mixture was stirred at −78° C. for 2 hours. To the reaction mixture, 1N hydrochloric acid was added. The mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated to give the title compound (0.22 g) having the following physical data.

Workup

  1. stirringThe mixture was stirred at room temperature for 30 minutes
  2. stirringThe mixture was stirred at −78° C. for 2 hours
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe extract was washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e814b6a82d1d473ca8ffe20b31941841
Source dataset
uspto-grants-2002_07
Patent number
US06420427B1

Reaction notes

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