HCID 54013766, compound → 5-Hydroxy-N-(1-{2-[hydroxy(imino)methyl]pyrrolidin-1-yl}-1-oxopentan-2-yl)-3,4-dihydro-2H-pyrrole-2-carboximidic acid

HRID 1155075Notes

Reaction equation

HRID 1155075 reaction equation
[N:1]1(C(OCC2C=CC=CC=2)=O)[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:14]([N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([NH2:20])=[O:19])=[O:15])[CH2:11][CH2:12][CH3:13])=[O:8].[H][H]>CO.[Pd]>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:14]([N:16]1[CH2:23][CH2:22][CH2:21][C@H:17]1[C:18]([NH2:20])=[O:19])=[O:15])[CH2:11][CH2:12][CH3:13])=[O:8]

Participants

5

Reactant 2

HCID 54013766HCID 54013766, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 1324895-Hydroxy-N-(1-{2-[hydroxy(imino)methyl]pyrrolidin-1-yl}-1-oxopentan-2-yl)-3,4-dihydro-2H-pyrrole-2-carboximidic acidYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.42 g (3.1 mmoles) of Z-Glp-Nva-Pro-NH2 are dissolved in 30 ml of methanol. 0.2 g of a 10% palladium-on-carbon catalyst are added to the solution, and hydrogen is bubbled through the mixture for 30 minutes. The catalyst is filtered off, the filtrate is evaporated, and the amorphous, solid residue is triturated with ether. The resulting crude product is dissolved in water, the solution is decolourized, filtered, and the clear filtrate is freeze-dried. 0.95 g (94%) of Glp-Nva-Pro-NH2 are obtained; Rf4 =0.36, [α]D25 =-87.0° (c=1%, in acetic acid). Amino acid analysis: Glu: 0.97 (1.0), Nva: 1.09 (1.0), Pro: 1.00 (1.0).

Workup

  1. customis bubbled through the mixture for 30 minutes
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customthe amorphous, solid residue is triturated with ether
  5. dissolutionThe resulting crude product is dissolved in water
  6. filtrationfiltered
  7. customthe clear filtrate is freeze-dried

Sources & evidence

ORD record
ord-a080d526b40d4a08b712a381b278c1de
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

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