HCID 86656625, compound → HCID 86656626, compound

HRID 882888Notes

Reaction equation

HRID 882888 reaction equation
C(OC(=O)[NH:7][C@H:8]([CH2:32][NH:33][C:34]([C:36]1[C:41]([NH2:42])=[N:40][C:39]([NH2:43])=[C:38]([Cl:44])[N:37]=1)=[O:35])[CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:31])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:19][CH:18]=1)(C)(C)C>O1CCOCC1.Cl>[ClH:44].[NH2:7][C@@H:8]([CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:14](=[O:31])[CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][C:20]([O:23][CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:21][CH:22]=1)[CH2:32][NH:33][C:34]([C:36]1[C:41]([NH2:42])=[N:40][C:39]([NH2:43])=[C:38]([Cl:44])[N:37]=1)=[O:35]

Participants

4

Reactant 1

HCID 86656625HCID 86656625, compound

Product 1

HCID 86656626HCID 86656626, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent2×

Procedure

A solution of ((S)-5-[3-(4-benzyloxy-phenyl)-propionylamino]-1-{[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-methyl}-pentyl)-carbamic acid tert-butyl ester (0.29 g, 0.45 mmol) in 1,4-dioxane (3 mL) and HCl (5 mL of a 4 M solution in 1,4-dioxane, 20 mmol) is stirred at RT for 2 h. The solvent is removed in vacuo and the resulting residue is triturated with diethyl ether and then the diethyl ether is decanted. The remaining solid is dissolved in a minimal amount of MeOH then diethyl ether is added to cause precipitation. The supernatant solvents are decanted and the remaining solid is washed with diethyl ether then dried under vacuum to afford the title compound as yellow solid. [M+H]+ 540.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe resulting residue is triturated with diethyl ether
  3. customthe diethyl ether is decanted
  4. dissolutionThe remaining solid is dissolved in a minimal amount of MeOH
  5. additiondiethyl ether is added
  6. customprecipitation
  7. customThe supernatant solvents are decanted
  8. washthe remaining solid is washed with diethyl ether
  9. customthen dried under vacuum

Sources & evidence

ORD record
ord-4c656c7c676c449182402ce73cc516b1
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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