Sodium Carbonate → HCID 12968764, compound

HRID 983645Notes

Reaction equation

HRID 983645 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:7]([NH:9][C@H:10]([C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].C([O-])([O-])=O.[Na+].[Na+]>CN1CCCC1=O.[Pd]>[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:18]([NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:5])[CH3:6]

Participants

5

Reactant 2

HCID 10340Sodium CarbonateHCID 131724778HCID 131724778, compound

Product 1

HCID 12968764HCID 12968764, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The organic layer containing Z-Leu-Phe-NH-(CH2)7-CH3 was diluted with 1-methyl-2-pyrrolidinone and subjected to catalytic hydrogenolysis in the presence of palladium on charcoal. Upon completion of the reaction, 5% Na2CO3/10% NaCl was added and the resulting suspension was filtered at 45° C. The residue was washed with ethyl acetate, and the combined organic filtrates were extracted with 5% Na2CO3/10% NaCl, 30% NaCl and water. The organic layer was evaporated to dryness to give the desired product in 85% yield.

Workup

  1. additionwas added
  2. filtrationthe resulting suspension was filtered at 45° C
  3. washThe residue was washed with ethyl acetate
  4. extractionthe combined organic filtrates were extracted with 5% Na2CO3/10% NaCl, 30% NaCl and water
  5. customThe organic layer was evaporated to dryness

Sources & evidence

ORD record
ord-f3b58eb09f184cf79e035c9480593bf5
Source dataset
uspto-grants-2005_03
Patent number
US06864357B2

Reaction notes

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