HCID 70502790, compound → HCID 54240251, compound

HRID 1903610Notes

Reaction equation

HRID 1903610 reaction equation
C(OC([NH:11][C@@H:12]([C:14]([NH:16][CH:17]([CH:21]1[CH2:25][C:24](=[O:26])[NH:23][C:22]1=[O:27])[C:18]([OH:20])=[O:19])=[O:15])[CH3:13])=O)C1C=CC=CC=1.[H][H]>O.CO.C(O)(=O)C.[Pd]>[NH2:11][C@@H:12]([C:14]([NH:16][CH:17]([CH:21]1[CH2:25][CH:24]([OH:26])[NH:23][C:22]1=[O:27])[C:18]([OH:20])=[O:19])=[O:15])[CH3:13]

Participants

5

Reactant 2

HCID 70502790HCID 70502790, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54240251HCID 54240251, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 86607755Acetic acid methanol waterSolvent

Procedure

In 100 ml of water-methanol-acetic acid (1:1:0.2) was dissolved 2.0 g of benzyloxycarbonyl-D-alanyl-2-(2,5-dioxopyrrolidin-3-yl)glycine, and the solution was stirred with 600 mg of palladium black in a stream of hydrogen at room temperature for 2 hours. The reaction mixture was filtered and the filtrate was concentrated to dryness under reduced pressure. The residue was dissolved in 70 ml of water and, following addition of 580 mg of sodium borohydride at 0°-5° C., the mixture was stirred for 30 minutes with adjusting pH to 8.5-9.2 with 2 N hydrochloric acid. This reaction mixture was adsorbed on a column (150 ml) of Amberlite IRA-68 (OH- -form) and after the column was washed with water, elution was carried out with 0.3 N acetic acid. The eluate was concentrated to dryness under reduced pressure and the resultant powder was subjected to column chromatography on activated carbon (250 ml) and eluted with water. The eluate was concentrated under reduced pressure and lyophilized to give D-alanyl-2-(5-hydroxy-2-oxopyrrolidin-3-yl)glycine as a white powder.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure
  3. dissolutionThe residue was dissolved in 70 ml of water
  4. additionaddition of 580 mg of sodium borohydride at 0°-5° C.
  5. wash(OH- -form) and after the column was washed with water, elution
  6. concentrationThe eluate was concentrated to dryness under reduced pressure
  7. washeluted with water
  8. concentrationThe eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-66358bbe2fb14d4098dd9a96a9a36ccf
Source dataset
uspto-grants-1984_03
Patent number
US04436918

Reaction notes

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