1,4-Dioxane hydrochloride → HCID 178479456, compound

HRID 1702113Notes

Reaction equation

HRID 1702113 reaction equation
[C:1]1([O:11][C:12](=[O:61])[C@H:13]([CH2:34][CH2:35][CH2:36][N:37](C(OCC2C=CC=CC=2)=O)[C:38](=[NH:50])[NH:39]C(OCC2C=CC=CC=2)=O)[NH:14][C:15](=[O:33])[C@H:16]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[ClH:62].O1CCOCC1.[H][H]>CN(C=O)C.[Pd]>[ClH:62].[C:1]1([O:11][C:12](=[O:61])[C@H:13]([CH2:34][CH2:35][CH2:36][NH:37][C:38](=[NH:39])[NH2:50])[NH:14][C:15](=[O:33])[C@H:16]([CH2:26][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[NH:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[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 178512414HCID 178512414, compound

Product 1

HCID 178479456HCID 178479456, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

In 10 ml of DMF was dissolved 1.07 g of the above ester, after which 0.5 g of 10% Pd-C and 1.65 ml of 2 N hydrochloric acid-dioxane solution were added thereto. The mixture was stirred with ice-cooling for 3 hrs while passing hydrogen gas therethrough. After the reaction, the reaction mixture was filtered to remove the Pd-C, and 500 ml of anhydrous diethyl ether was added to the filtrate. The white powder thus precipitated was collected and vacuum-dried over P2O5 at 110° C. for 3 hrs to obtain 700 mg (yield 92%) of benzoyl-L-phenylalanyl-L-arginine 1-naphthyl ester hydrochloride, m.p. 112° C.-(decomp.).

Workup

  1. temperaturecooling for 3 hrs
  2. customAfter the reaction
  3. filtrationthe reaction mixture was filtered
  4. customto remove the Pd-C, and 500 ml of anhydrous diethyl ether
  5. additionwas added to the filtrate
  6. customThe white powder thus precipitated
  7. customwas collected
  8. dry with materialvacuum-dried over P2O5 at 110° C. for 3 hrs

Sources & evidence

ORD record
ord-c17eaef623144cb59ac7133f82144e9b
Source dataset
uspto-grants-1983_04
Patent number
US04379764

Reaction notes

Loading…