1,4-Dioxane hydrochloride → HCID 178478815, compound

HRID 1702111Notes

Reaction equation

HRID 1702111 reaction equation
[C:1]1([O:11][C:12](=[O:63])[C@H:13]([CH2:36][CH2:37][CH2:38][N:39](C(OCC2C=CC=CC=2)=O)[C:40](=[NH:52])[NH:41]C(OCC2C=CC=CC=2)=O)[NH:14][C:15](=[O:35])[C@H:16]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[NH:17]C(OCC2C=CC=CC=2)=O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[ClH:64].O1CCOCC1.[H][H]>CN(C=O)C.[C].[Pd]>[ClH:64].[ClH:64].[C:1]1([O:11][C:12](=[O:63])[C@H:13]([CH2:36][CH2:37][CH2:38][NH:39][C:40](=[NH:41])[NH2:52])[NH:14][C:15](=[O:35])[C@H:16]([CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[NH2:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 204431481,4-Dioxane hydrochlorideHCID 178418361HCID 178418361, compoundHCID 178512415HCID 178512415, compound

Product 1

HCID 178478815HCID 178478815, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

In DMF was dissolved 935 mg of the above ester, and to the resulting solution were added 0.5 g of 10% palladium-carbon (Pd-C) and 0.98 ml of a 2 N hydrochloric acid-dioxane solution, after which hydrogen gas was passed through the resulting mixture with ice-cooling and with stirring for 4 hrs. After the reaction, the Pd-C was removed by filtration, and 300 ml of anhydrous diethyl ether was added dropwise to the filtrate, upon which a powder was precipitated. The powder was collected by filtration to obtain 450 mg (yield 78%) of L-phenylalanyl-L-arginine 1-naphthyl ester dihydrochloride, m.p. 215° C. (decomp.).

Workup

  1. temperaturecooling
  2. customAfter the reaction
  3. customthe Pd-C was removed by filtration, and 300 ml of anhydrous diethyl ether
  4. additionwas added dropwise to the filtrate, upon which a powder
  5. customwas precipitated
  6. filtrationThe powder was collected by filtration

Sources & evidence

ORD record
ord-e8fc733fff1c45b195ff1aa521046cc2
Source dataset
uspto-grants-1983_04
Patent number
US04379764

Reaction notes

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