Hydrochloric Acid → HCID 54261631, compound

HRID 369553Notes

Reaction equation

HRID 369553 reaction equation
O.[OH-].[Li+].C[O:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([N:20]([CH3:22])[CH3:21])[C:17]([O:23][C@H:24]([CH3:31])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[CH:16][C:15]=2[N+:32]([O-:34])=[O:33])=[CH:10][CH:9]=1)=[O:7].C1COCC1.Cl>CO.O>[N+:32]([C:15]1[CH:16]=[C:17]([O:23][C@H:24]([CH3:31])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:18]([N:20]([CH3:21])[CH3:22])=[CH:19][C:14]=1[C:11]1[CH:12]=[CH:13][C:8]([C:6]([OH:7])=[O:5])=[CH:9][CH:10]=1)([O-:34])=[O:33]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 54560925HCID 54560925, compound

Product 1

HCID 54261631HCID 54261631, compoundYield 103.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Lithium hydroxide monohydrate (96 mg, 2.28 mmol) was added to a stirred solution of compound 64 (49 mg, 0.11 mmol), THF (2 ml), water (3 ml), and methanol (10 ml). The reaction mixture was refluxed overnight and then was acidified with concentrated HCl. The reaction mixture was extracted twice with dichloromethane, the combined organic layers were washed with brine and dried over MgSO4. Evaporation of solvent yielded 47 mg (100%) of a yellow solid. The crude product was carried on without purification.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. extractionThe reaction mixture was extracted twice with dichloromethane
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of solvent

Sources & evidence

ORD record
ord-d670ae772c32481fa6f87e30ac1053e8
Source dataset
uspto-grants-2000_10
Patent number
US06139771

Reaction notes

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