Hydrochloric Acid → HCID 46185508, compound

HRID 561973Notes

Reaction equation

HRID 561973 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][C@@H:8]1[C:12](=[O:13])[N:11]([C@H:14]([C:23]2[NH:24][C:25]([C:28]3[CH:33]=[CH:32][C:31]([I:34])=[CH:30][CH:29]=3)=[CH:26][N:27]=2)[C@H:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:16])[C:10](=[O:35])[NH:9]1)(C)(C)C.Cl.O1CCOCC1>>[I:34][C:31]1[CH:30]=[CH:29][C:28]([C:25]2[NH:24][C:23]([C@@H:14]([N:11]3[C:12](=[O:13])[C@@H:8]([CH2:7][C:6]([OH:36])=[O:5])[NH:9][C:10]3=[O:35])[C@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[N:27][CH:26]=2)=[CH:33][CH:32]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67001707HCID 67001707, compound

Product 1

HCID 46185508HCID 46185508, compound

Procedure

To ((R)-1-{(1S,2S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-2,5-dioxo-imidazolidin-4-yl)-acetic acid tert-butyl ester (120 mg, 0.2 mmol) was added 4 N hydrogen chloride in p-dioxane (2 mL, 0.8 mmol). The mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo and hexane was added to form a precipitate. The solid was collected by filtration and dried to give ((R)-1-{(1S,2S)-1-[5-(4-iodo-phenyl)-1H-imidazol-2-yl]-2-phenyl-propyl}-2,5-dioxo-imidazolidin-4-yl)-acetic acid; hydrochloride salt as a light yellow solid (120 mg, 100%). LC-MS: calcd for C23H21IN4O4 [M+H+] 545. Found 545.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo and hexane
  2. additionwas added
  3. customto form a precipitate
  4. filtrationThe solid was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-1c881b094a17465eb02ac3de6dc26848
Source dataset
uspto-grants-2011_11
Patent number
US08063085B2

Reaction notes

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