Hydrochloric Acid → HCID 178519553, compound

HRID 1873589Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH:7]1[C:11]([C:12]2[CH:13]=[C:14]([CH:19]=[CH:20][CH:21]=2)[C:15](OC)=[O:16])=[N:10][N:9]=[N:8]1.Cl.[H][H]>C1COCC1>[NH:10]1[C:11]([C:12]2[CH:13]=[C:14]([CH2:15][OH:16])[CH:19]=[CH:20][CH:21]=2)=[N:7][N:8]=[N:9]1

Participants

Conditions

Temperature: 0 °C

Procedure

438 mg (11.56 mmol) of lithium aluminum hydride are initially charged in 60 ml of dry THF and cooled to 0° C., and a solution of 1.18 g (5.78 mmol) of the compound from Example 48A in 40 ml of dry THF is added. The reaction mixture is allowed to warm to RT and stirred at this temperature for 2 h. At 0° C., 4 M hydrochloric acid is added carefully to the reaction mixture until the evolution of hydrogen has stopped. The solution is then extracted three times with in each case 10 ml of ethyl acetate. The combined organic phases are washed in each case once with in each case 10 ml of water and saturated aqueous sodium chloride solution and dried over magnesium sulfate. After removal of the solvent on a rotary evaporator the residue is dried under reduced pressure. The product is used in the next reaction without further purification.

Workup

temperatureto warm to RT
extractionThe solution is then extracted three times with in each case 10 ml of ethyl acetate
washThe combined organic phases are washed in each case once with in each case 10 ml of water and saturated aqueous sodium chloride solution
dry with materialdried over magnesium sulfate
customAfter removal of the solvent
customon a rotary evaporator the residue
customis dried under reduced pressure
customThe product is used in the next reaction without further purification

Sources & evidence

ORD record: ord-1c0418f3ede5410286907e7eada76759
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08304412B2

Reaction notes

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