HCID 131712540, compound → 5-Oxo-L-prolyl-L-threonyl-L-prolinamide

HRID 1155080Notes

Reaction equation

HRID 1155080 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:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([NH2:27])=[O:26])=[O:22])[C@@H:11]([CH3:20])[O:12]CC1C=CC=CC=1)=[O:8]>C(O)(=O)C.[Pd]>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:21]([N:23]1[CH2:30][CH2:29][CH2:28][C@H:24]1[C:25]([NH2:27])=[O:26])=[O:22])[C@@H:11]([CH3:20])[OH:12])=[O:8]

Participants

4

Reactant 1

HCID 131712540HCID 131712540, compound

Product 1

HCID 228184355-Oxo-L-prolyl-L-threonyl-L-prolinamideYield 59.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2.04 g (3.7 mmoles) of Z-Glp-Thr(Bzl)-Pro-NH2 are dissolved in 40 ml of acetic acid, 0.4 g of a 10% palladium-on-carbon catalyst are added, and hydrogen is bubbled through the mixture for 4 hours. The catalyst is filtered off, the filtrate is evaporated, and the residue is triturated with ether. The resulting 1.31 g of amorphous crude product are applied onto the top of a column filled with 30 g of silica gel (particle size: 0.063-0.2 mm), and the column is eluted with solvent mixture (3). The main fractions which contain the pure substance are combined, evaporated, and the product is isolated with ether. 0.72 g (59.5%) of Glp-Thr-Pro-NH2 are obtained; Rf4 =0.16, [α]D25 =-90.0° (c=1%, in acetic acid). Amino acid analysis: Glu: 1.00 (1.0), Thr: 0.99 (1.0), Pro: 1.03 (1.0).

Workup

  1. customhydrogen is bubbled through the mixture for 4 hours
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customthe residue is triturated with ether
  5. additionfilled with 30 g of silica gel (particle size: 0.063-0.2 mm)
  6. washthe column is eluted with solvent mixture (3)
  7. customevaporated
  8. customthe product is isolated with ether

Sources & evidence

ORD record
ord-56edfb7dde9d4352a462b5b1ceb2467d
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

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