HCID 131712541, compound → HCID 13312523, compound

HRID 1155081Notes

Reaction equation

HRID 1155081 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:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([NH2:23])=[O:22])=[O:18])[CH2:11][O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:8]>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:17]([N:19]1[CH2:26][CH2:25][CH2:24][C@H:20]1[C:21]([NH2:23])=[O:22])=[O:18])[CH2:11][O:12][C:13]([CH3:16])([CH3:14])[CH3:15])=[O:8]

Participants

4

Reactant 1

HCID 131712541HCID 131712541, compound

Product 1

HCID 13312523HCID 13312523, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4.02 g (8 mmoles) of Z-Glp-Ser(tBu)-Pro-NH2 are dissolved in 160 ml of methanol, 0.8 g of a 10% palladium-on-carbon catalyst are added, and hydrogen is bubbled through the mixture for 30 minutes. The catalyst is filtered off, the filtrate is evaporated, and the residue is covered with ether and allowed to crystallize. The crystals are filtered off to obtain 2.50 g (85%) of Glp-Ser(tBu)-Pro-NH2 ; m.p.: 186°-187° C., Rf4 =0.45, [α]D25 =-60.8° (c=1%, in acetic acid). Amino acid analysis: Glu: 1.03 (1.0), Ser: 1.00 (1.0), Pro: 1.00 (1.0).

Workup

  1. customhydrogen is bubbled through the mixture for 30 minutes
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customto crystallize
  5. filtrationThe crystals are filtered off

Sources & evidence

ORD record
ord-de3a23e15f7c4cb892cc97a8afac8956
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

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