Hydrochloric Acid → HCID 131718745, compound

HRID 1708335Notes

Reaction equation

HRID 1708335 reaction equation
[CH2:1]1[CH:16]2[CH:5]([NH:6][C:7](=O)[CH2:8][NH:9][CH:10]3[CH2:21][CH:20]=[CH:19][CH2:18][CH:11]3[NH:12][CH2:13][C:14](=O)[NH:15]2)[CH2:4][CH2:3][CH2:2]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O)C.[ClH:32]>O1CCCC1.C(OCC)C.CCCCCC>[ClH:32].[ClH:32].[ClH:32].[CH2:21]1[CH:10]2[CH:11]([NH:12][CH2:13][CH2:14][NH:15][CH:16]3[CH2:1][CH:2]=[CH:3][CH2:4][CH:5]3[NH:6][CH2:7][CH2:8][NH:9]2)[CH2:18][CH2:19][CH2:20]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 18958573HCID 18958573, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 131718745HCID 131718745, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A mixture containing compound (C) (3.45 g., 11.3 mmol.) and 1M L/A/H4 (40ml.) in tetrahydrofuran (100 ml.) was refluxed for 21 hours under a dry nitrogen atmosphere. The solution was cooled and the excess LAH was decomposed by the careful addition of a saturated aqueous solution of Rochelles's salt (10 ml.). Absolute ethanol (50 ml.) was added to the suspension and the mixture was refluxed overnight. After filtration, the residual product in the filter cake was extracted by treatment of the solid with hot ethanol (2×100 ml.). The filtrates were combined and evaporated to afford 4.0 g. of a brownish mass. Crystallization from acetonitrile gave off-white crystals which dissolved in ethyl ether and hexane washes. A portion of this material (400 mg., 1.6 mmol.) was converted to the hydrochloride salt by treatment with methanolic hydrochloric acid (7 ml.).

Workup

  1. temperaturewas refluxed for 21 hours under a dry nitrogen atmosphere
  2. temperatureThe solution was cooled
  3. temperaturethe mixture was refluxed overnight
  4. filtrationAfter filtration
  5. extractionthe residual product in the filter cake was extracted by treatment of the solid with hot ethanol (2×100 ml.)
  6. customevaporated
  7. customto afford 4.0 g
  8. customCrystallization from acetonitrile
  9. customgave off-white crystals which

Sources & evidence

ORD record
ord-ddf28c7332184c4bb45f9052620cb0eb
Source dataset
uspto-grants-1994_10
Patent number
US05358704

Reaction notes

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