Potassium → HCID 53765055, compound

HRID 1600846Notes

Reaction equation

HRID 1600846 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([NH:18][C@H:19]([C:35](O)=[O:36])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[CH:23][CH:22]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[K]>C(OCC)C.C1COCC1>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([NH:18][C@H:19]([CH:35]=[O:36])[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[CH:25][CH:26]=1)=[O:17])[CH:13]([CH3:14])[CH3:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 5462222PotassiumHCID 21226445Aluminium lithium hydrideHCID 26299933HCID 26299933, compound

Product 1

HCID 53765055HCID 53765055, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-benzyloxycarbonyl-L-valyl-O-benzyl-L-tyrosine, N,O-dimethylhydroxamate (8.90 g, 16.2 mmol) in anhydrous diethyl ether (150 ml) and anhydrous THF (20 ml) at 0° C. is added lithium aluminum hydride (0.67 g, 17.7 mmol). The mixture is stirred at 0° C. for 1 hour. A solution of 1M potassium hydrogenosulphate (25 ml) is then added with precaution. The organic layer is separated and the aqueous phase is extracted twice with ethyl acetate (2×100 ml). The combined organic layers are then washed with a 3N solution of hydrochloric acid (30 ml), water (30 ml) and brine (30 ml), and dried over anhydrous magnesium sulphate. Filtration and evaporation of the solvent in vacuo affords a white solid which is recrystallized in ethylacetate/pentane to give the title compound (5.40 g, 68% yield).

Workup

  1. customThe organic layer is separated
  2. extractionthe aqueous phase is extracted twice with ethyl acetate (2×100 ml)
  3. washThe combined organic layers are then washed with a 3N solution of hydrochloric acid (30 ml), water (30 ml) and brine (30 ml)
  4. dry with materialdried over anhydrous magnesium sulphate
  5. filtrationFiltration and evaporation of the solvent in vacuo
  6. customaffords a white solid which
  7. customis recrystallized in ethylacetate/pentane

Sources & evidence

ORD record
ord-860613ca2c2f416ebe910626bda20786
Source dataset
uspto-grants-1999_11
Patent number
US05977074

Reaction notes

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