Hydrochloric Acid → HCID 69712160, compound

HRID 2121899Notes

Reaction equation

HRID 2121899 reaction equation
C([O:5][C:6](=O)[CH2:7][O:8][C@H:9]1[CH2:27][O:26][C:12]2=[CH:13][CH:14]=[C:15]3[C:19]([N:18]([CH2:20][C@@H:21]([N:23]=[N+]=[N-])[CH3:22])[N:17]=[CH:16]3)=[C:11]2[CH2:10]1)(C)(C)C.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.[ClH:37]>C1COCC1>[ClH:37].[ClH:37].[NH2:23][C@@H:21]([CH3:22])[CH2:20][N:18]1[C:19]2[C:15](=[CH:14][CH:13]=[C:12]3[O:26][CH2:27][C@H:9]([O:8][CH2:7][CH2:6][OH:5])[CH2:10][C:11]3=2)[CH:16]=[N:17]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 21226445Aluminium lithium hydrideHCID 131724352HCID 131724352, compound

Product 1

HCID 69712160HCID 69712160, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of the product from Step C (0.30 g, 0.78 mmol) in anhydrous THF (20 mL) under nitrogen was added a 1 M solution of lithium aluminum hydride in THF (2.0 mL, 2.6 mmol). The mixture was stirred for 1 h and cooled followed by the addition of methanol and 2 N HCl. The volatiles were evaporated and the residue was purified by reversed phase HPLC (gradient, 0% to 50% acetonitrile in water). The desired fractions were combined, concentrated, treated with 2 N HCl in ethanol (10 mL), and evaporated (in vacuo, 65° C.) to give a glass (0.17 g, 59%): mp>100° C.; LCMS (+APCI) m/z 292 (M+H).

Workup

  1. temperaturecooled
  2. customThe volatiles were evaporated
  3. customthe residue was purified by reversed phase HPLC (gradient, 0% to 50% acetonitrile in water)
  4. concentrationconcentrated
  5. additiontreated with 2 N HCl in ethanol (10 mL)
  6. customevaporated (in vacuo, 65° C.)

Sources & evidence

ORD record
ord-4e1f158ff04f4a289c5236416f9cf18e
Source dataset
uspto-grants-2004_02
Patent number
US06696476B2

Reaction notes

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