Hydrogen Bromide → HCID 22795868, compound

HRID 1834145Notes

Reaction equation

HRID 1834145 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:17]2[C:21]([CH2:22][NH:23][C:24](=[O:41])[C@H:25]([CH2:37][CH:38]([CH3:40])[CH3:39])[NH:26]C(OCC3C=CC=CC=3)=O)=[CH:20][N:19]=[CH:18]2)=[C:6]([CH:16]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15])=[O:8].[BrH:42].[CH2:43](OCC)C>C(O)(=O)C>[BrH:42].[BrH:42].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:17]2[C:21]([CH2:22][NH:23][C:24](=[O:41])[C@H:25]([CH2:37][CH:38]([CH3:39])[CH3:40])[NH2:26])=[CH:20][N:19]=[C:18]2[CH3:43])=[C:6]([CH:16]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15])=[O:8]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 54359178HCID 54359178, compound

Product 1

HCID 22795868HCID 22795868, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

0.40 g of 5-chloro-2'-fluoro-2-[5-[(N-benzyloxycarbonyl-L-leucyl)aminomethyl]-1-imidazolyl]benzophenone was treated with a 35% solution of hydrogen bromide in glacial acetic acid for 45 minutes. Dry diethyl ether was then added, an oily solid being obtained. The product was precipitated from methanol/ethyl acetate, dissolved in water and freeze-dried. There was obtained 5-chloro-2'-fluoro-2-[5-(L-leucylaminomethyl)-2-methyl-1-imidazolyl]benzophenone dihydrobromide in a yield of 0.25 g (60%); [α]D20 = -5.5° (c = 0.2708 in water).

Workup

  1. customan oily solid being obtained
  2. customThe product was precipitated from methanol/ethyl acetate
  3. dissolutiondissolved in water
  4. customfreeze-dried

Sources & evidence

ORD record
ord-20534c3b411441c0b62a32bf5fba08f1
Source dataset
uspto-grants-1978_01
Patent number
US04069229

Reaction notes

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