Sodium Hydroxide → HCID 178512039, compound

HRID 1418855Notes

Reaction equation

HRID 1418855 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[C:6]([NH:10][C:11]([N:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[NH:12])[CH:7]=[CH:8][CH:9]=1.[C:18](=O)(O)[O-].[Na+].[NH:23]([C:35]([O:37][C:38]([CH3:41])(C)C)=[O:36])[CH2:24][C:25]([O:27]N1C(=O)CCC1=O)=O.O[CH:43]([CH2:47][C:48]([O-])=O)[C:44]([O-])=O.[OH-].[Na+]>O.O1CCOCC1.C(OCC)(=O)C.CCCCCC>[C:41]1([CH2:38][O:37][C:35]([NH:23][CH2:24][C:25]([NH:3][C:4]2[CH:5]=[C:6]([NH:10][C:11]([N:13]3[CH2:17][CH2:16][CH2:15][CH2:14]3)=[NH:12])[CH:7]=[CH:8][CH:9]=2)=[O:27])=[O:36])[CH:18]=[CH:48][CH:47]=[CH:43][CH:44]=1

Participants

10

Reactant 5

HCID 14798Sodium HydroxideHCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 160434DL-MalateHCID 516892Sodium BicarbonateHCID 178478772HCID 178478772, compound

Product 1

HCID 178512039HCID 178512039, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the product of Example 1, step (b) (1.0 g; 0.0036 moles) in 5.0 ml of water and 5.0 ml of dioxane was added sodium bicarbonate (0.15 g; 0.0018 moles) the reaction then cooled to 0° C. To the stirred solution was added the compound Boc-Gly-OSu, wherein Boc represents benzyloxycarbonyl and OSu represents hydroxysuccinate, (1.1 g; 0.0036 moles) (Novabiochem) and the reaction allowed to warm to room temperature for 18 hrs. The reaction was then poured into 75 ml of water and 20 ml of 2N sodium hydroxide. The aqueous phase was then extracted 3×50 ml of ethyl acetate, and the combined organic extracts were dried over magnesium sulfate. Evaporation of the solvent gave a crude solid which was slurried in 25 ml of ethyl acetate and 75 ml of hexane. The resulting solids were collected by filtration and dried at 20° C. for 24 hrs to give N-(3-(((((phenylmethoxy)carbonyl)amino)methyl)carbonyl)aminophenyl)-1-pyrrolidinecarboximidamide, M.P. 81°-82° C.

Workup

  1. customthe reaction
  2. temperatureto warm to room temperature for 18 hrs
  3. extractionThe aqueous phase was then extracted 3×50 ml of ethyl acetate
  4. dry with materialthe combined organic extracts were dried over magnesium sulfate
  5. customEvaporation of the solvent
  6. customgave a crude solid which
  7. filtrationThe resulting solids were collected by filtration
  8. customdried at 20° C. for 24 hrs

Sources & evidence

ORD record
ord-85ceeb8b8d074d0a890349a5c043d8a3
Source dataset
uspto-grants-1999_03
Patent number
US05885985

Reaction notes

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