Ammonium formate → HCID 13384499, compound

HRID 1253097Notes

Reaction equation

HRID 1253097 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:4]([NH:6][C@H:7]([C@H:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[OH:13])[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:5])[CH3:3].C([O-])=O.[NH4+]>CO.[Pd]>[NH2:1][C@H:2]([C:4]([NH:6][C@H:7]([C@H:12]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[OH:13])[CH2:8][CH:9]([CH3:10])[CH3:11])=[O:5])[CH3:3]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 13384497HCID 13384497, compound

Product 1

HCID 13384499HCID 13384499, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

1.46 g of Z-Ala-Sta-OMe are dissolved in 20 ml of MeOH, 1.03 g of ammonium formate are then added at RT, the mixture is stirred until a solution forms, 400 mg of 10% Pd/C are then added and the mixture is stirred for 5 min at RT. After 5 min, checking by TLC shows that the starting material has disappeared. The pH is 8 to pH paper. The whole mixture is filtered on celite and then the methanolic solution is filtered on a column of Amberlite IR 45 resin (OH) and the methanol is evaporated off. The residue is taken up in ether, the mixture is evaporated to dryness, the residue is then dissolved in CH2Cl2, the insoluble material is filtered off and the filtrate is evaporated to dryness to give a white powder.

Workup

  1. additionare then added
  2. waitAfter 5 min
  3. filtrationThe whole mixture is filtered on celite
  4. filtrationthe methanolic solution is filtered on a column of Amberlite IR 45 resin (OH)
  5. customthe methanol is evaporated off
  6. customthe mixture is evaporated to dryness
  7. dissolutionthe residue is then dissolved in CH2Cl2
  8. filtrationthe insoluble material is filtered off
  9. customthe filtrate is evaporated to dryness
  10. customto give a white powder

Sources & evidence

ORD record
ord-cfb8ae7e6d39440c891160234ec682b0
Source dataset
uspto-grants-1988_05
Patent number
US04746648

Reaction notes

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