Hydrochloric Acid → HCID 178479361, compound

HRID 77520Notes

Reaction equation

HRID 77520 reaction equation
[Cl-:1].C([O:6][C:7]([C@@H:9]([NH:17][C:18]([CH2:20][N+:21]12[CH2:28][CH2:27][CH:24]([CH2:25][CH2:26]1)[C@H:23]([NH:29][C:30]([NH2:43])=[N:31][C:32]([C:34]1[C:39]([NH2:40])=[N:38][C:37]([NH2:41])=[C:36]([Cl:42])[N:35]=1)=[O:33])[CH2:22]2)=[O:19])[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])(C)(C)C.Cl>C(OCC)C>[ClH:42].[Cl-:1].[C:7]([C@@H:9]([NH:17][C:18]([CH2:20][N+:21]12[CH2:28][CH2:27][CH:24]([CH2:25][CH2:26]1)[C@H:23]([NH:29][C:30]([NH2:43])=[N:31][C:32]([C:34]1[C:39]([NH2:40])=[N:38][C:37]([NH2:41])=[C:36]([Cl:42])[N:35]=1)=[O:33])[CH2:22]2)=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([OH:8])=[O:6]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178451188HCID 178451188, compound2×

Product 1

HCID 178479361HCID 178479361, compoundYield 114.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 140 mg (0.22 mmol) (S)-1-[((S)-1-tert-butoxycarbonyl-2-phenyl-ethylcarbamoyl)-methyl]-3-[N′-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-guanidino]-1-azonia-bicyclo-[2.2.2]-octane chloride (Intermediate 59) and 6.2 mL (12.4 mmol) HCl (2 M) in diethyl ether is stirred overnight at room temperature. The resulting solid is collected by filtration and washed with diethyl ether. Recrystallization from acetone yields the title compound (78 mg).

Workup

  1. filtrationThe resulting solid is collected by filtration
  2. washwashed with diethyl ether
  3. customRecrystallization from acetone

Sources & evidence

ORD record
ord-ae739132a620495d93c782a5262e5c44
Source dataset
uspto-grants-2014_09
Patent number
US08841309B2

Reaction notes

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