Aluminium lithium hydride → HCID 178479442, compound

HRID 986383Notes

Reaction equation

HRID 986383 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[ClH:7].[C:8]([NH:27][C@H:28]([C:36](O)=[O:37])[CH2:29][CH2:30][CH2:31][NH:32][C:33](=[NH:35])[NH2:34])([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O1CCCC1>[ClH:7].[C:8]([NH:27][C@H:28]([CH2:36][OH:37])[CH2:29][CH2:30][CH2:31][NH:32][C:33](=[NH:34])[NH2:35])([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 178479451HCID 178479451, compound

Product 1

HCID 178479442HCID 178479442, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

4.2 g of lithium aluminum hydride were suspended in 150 ml of absolute tetrahydrofuran and cooled to 0° C. in an ice bath. 9.3 g of the methyl ester of tritylarginine hydrochloride, which were dissolved in 50 ml of absolute tetrahydrofuran, were slowly added dropwise to this suspension. The mixture was stirred at 0° C. for 30 min and then heated to 40°-45° C. After 30 min, the excess lithium aluminum hydride was decomposed with ice-water. Insolubles were removed by filtration, and the tetrahydrofuran was substantially removed by evaporation. The residue was neutralised with 0.1 N hydrochloric acid, taken up in n-butanol/ethyl acetate (1:1 parts by volume) and the solution was washed with water. After removal of the organic solvent by evaporation, tritylargininol hydrochloride was obtained in the form of a foam.

Workup

  1. additionwere slowly added dropwise to this suspension
  2. temperatureheated to 40°-45° C
  3. waitAfter 30 min
  4. customInsolubles were removed by filtration
  5. customthe tetrahydrofuran was substantially removed by evaporation
  6. washthe solution was washed with water
  7. customAfter removal of the organic solvent
  8. customby evaporation

Sources & evidence

ORD record
ord-a8a441ceb05748b49028e68ab55d3cac
Source dataset
uspto-grants-1987_12
Patent number
US04713369

Reaction notes

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