Hydrochloric Acid → HCID 68215386, compound

HRID 1662041Notes

Reaction equation

HRID 1662041 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:29]([O:31]C)=[O:30])[NH:16][C:17]([C:19]1[N:20]([CH3:28])[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1.[OH-].[Na+].Cl>CO>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:29]([OH:31])=[O:30])[NH:16][C:17]([C:19]1[N:20]([CH3:28])[C:21]2[C:26]([CH:27]=1)=[CH:25][CH:24]=[CH:23][CH:22]=2)=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86644623HCID 86644623, compound

Product 1

HCID 68215386HCID 68215386, compoundYield 90.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of methyl N5-[(benzyloxy)carbonyl]-N2-[(1-methyl-1H-indol-2-yl)carbonyl]-L-ornithinate (13.2 g), THF (65 ml), and methanol (65 ml) was added a 1 M aqueous sodium hydroxide solution (60 ml) under ice-cooling, followed by stirring at room temperature for 3 hours. To the reaction mixture was added 1 M hydrochloric acid (60 ml) under ice-cooling, and the solvent was removed by evaporation under reduced pressure. The residue was stirred at room temperature for 14 hours, and the solid precipitated was collected by filtration and washed with water to obtain N5-[(benzyloxy)carbonyl]-N2-[(1-methyl -1H-indol-2-yl)carbonyl]-L-ornithine (11.6 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. customthe solvent was removed by evaporation under reduced pressure
  4. stirringThe residue was stirred at room temperature for 14 hours
  5. customthe solid precipitated
  6. filtrationwas collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-b07850bd998b47bd99394f1d014572af
Source dataset
uspto-grants-2011_10
Patent number
US08030489B2

Reaction notes

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