Hydrochloric Acid → HCID 178455930, compound

HRID 1086118Notes

Reaction equation

HRID 1086118 reaction equation
[OH-].[Na+].[NH:3]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[C@@H:4]([C:12]([NH:14][C@H:15]([C:20]([O:22]CC1C=CC=CC=1)=[O:21])[C@H:16]([CH2:18][CH3:19])[CH3:17])=[O:13])[CH2:5][CH2:6][CH2:7][NH:8][C:9](=[NH:11])[NH2:10].O.Cl>O1CCOCC1.CO>[NH:3]([C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31])[C@@H:4]([C:12]([NH:14][C@H:15]([C:20]([OH:22])=[O:21])[C@H:16]([CH2:18][CH3:19])[CH3:17])=[O:13])[CH2:5][CH2:6][CH2:7][NH:8][C:9](=[NH:10])[NH2:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 178455931HCID 178455931, compound

Product 1

HCID 178455930HCID 178455930, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

41.8 ml of aqueous 1N NaOH are added to a solution of 19 g of Z-D-Arg-Ile-OBzl in a mixture of 70 ml of dioxane, 30 ml of water and 12 ml of methanol, and the mixture is left to stand at room temperature overnight. The next day it is neutralized with about 3.3 ml of 4N HCl. The cloudy solution is filtered with suction through a clarifying layer, and the filtrate is concentrated. The residue is partitioned between 120 ml of n-pentanol and 120 ml of water. The aqueous phase is extracted a further 4 times by shaking with n-pentanol. The n-pentanol phases are concentrated together. The residue is triturated with ethyl acetate, and the precipitate is filtered off with suction.

Workup

  1. waitthe mixture is left
  2. filtrationThe cloudy solution is filtered with suction through a clarifying layer
  3. concentrationthe filtrate is concentrated
  4. customThe residue is partitioned between 120 ml of n-pentanol and 120 ml of water
  5. extractionThe aqueous phase is extracted a further 4 times
  6. concentrationThe n-pentanol phases are concentrated together
  7. customThe residue is triturated with ethyl acetate
  8. filtrationthe precipitate is filtered off with suction

Sources & evidence

ORD record
ord-c723acec83794fd896d6f22530792632
Source dataset
uspto-grants-1991_04
Patent number
US05011825

Reaction notes

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