Hydrochloric Acid → HCID 13035316, compound

HRID 358308Notes

Reaction equation

HRID 358308 reaction equation
Br.[NH2:2][C@H:3]([C:5]([NH:7][CH:8]([CH:12]1[CH2:16][C:15](=[O:17])[NH:14][C:13]1=[O:18])[C:9]([OH:11])=[O:10])=[O:6])[CH3:4].C(=O)([O-])O.[Na+].[BH4-].[Na+].Cl>O>[NH2:2][C@H:3]([C:5]([NH:7][CH:8]([CH:12]1[CH2:16][CH:15]([OH:17])[NH:14][C:13]1=[O:18])[C:9]([OH:11])=[O:10])=[O:6])[CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 70502727HCID 70502727, compound

Product 1

HCID 13035316HCID 13035316, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

In 20 ml of water was dissolved 3.2 g of L-alanyl-2-(2,5-dioxopyrrolidin-3-yl)glycine hydrobromide and the solution was adjusted to pH 6 with a saturated aqueous solution of sodium hydrogen carbonate and cooled to 0°-5° C. To this solution was added 1.5 g of sodium borohydride all at once. The mixture was stirred at the same temperature for one hour, while kept maintaining at pH 8.9-9.2 with 2 N hydrochloric acid. The reaction mixture was adjusted to pH 4.0 with 2 N hydrochloric acid, diluted with 200 ml of water and absorbed on a column (150 ml) of Amberlite IRA-68 (OH- -form). After the column was washed with water, elution was carried out with 0.2 N acetic acid. The eluate was concentrated to dryness under reduced pressure and the resultant powder was subjected to column chromatography on activated carbon and eluted with water. The eluate was concentrated under reduced pressure and lyophilized to give L-alanyl-2-(5-hydroxy-2-oxopyrrolidin-3-yl)glycine as a white powder.

Workup

  1. temperaturecooled to 0°-5° C
  2. customabsorbed on a column (150 ml) of Amberlite
  3. washAfter the column was washed with water, elution
  4. concentrationThe eluate was concentrated to dryness under reduced pressure
  5. washeluted with water
  6. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-384af7a26e4c4377b6d4b96d6d0edabf
Source dataset
uspto-grants-1984_08
Patent number
US04465844

Reaction notes

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