Hydrogen Bromide → HCID 131717708, compound

HRID 1646275Notes

Reaction equation

HRID 1646275 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([S:22][CH2:23][CH2:24][CH2:25][C:26]([NH:28][C@H:29]([C:45]([O:47][CH3:48])=[O:46])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34]C(OCC3C=CC=CC=3)=O)=[O:27])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.[BrH:49]>C(O)(=O)C.C(OCC)C>[BrH:49].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[C:11]([S:22][CH2:23][CH2:24][CH2:25][C:26]([NH:28][C@H:29]([C:45]([O:47][CH3:48])=[O:46])[CH2:30][CH2:31][CH2:32][CH2:33][NH2:34])=[O:27])[NH:12][C:13]=2[C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 131717710HCID 131717710, compound

Product 1

HCID 131717708HCID 131717708, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 3283Diethyl EtherSolvent

Procedure

The N2-[4-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]-1-oxobutyl]-N6-[(phenylmethoxy)carbonyl]-L-lysine, methyl ester (1.60 g, 0.0023 mol) was dissolved in hydrogen bromide 30 wt. % solution in acetic acid (20 ml) under a nitrogen atmosphere at ambient temperature. The reaction mixture was stirred for 1 hour, and diluted with ethyl ether to precipitate a gum. This residue was triturated with ethyl ether to give the title compound (1.58 g, 0.00224 mol, 95% yield) as an off white powder, mp 165°-70°. 1H NMR (DMSO-d6) δ8.38 (d, 1H), 7.80-7.70(bs, 3H), 7.39(d, 4H), 7.03(d, 4H), 4.26-4.23(m, 1H), 3.79(s, 6H), 3.6(s, 3H), 3.30-3.26(t, 2H), 2.79-2.73(m, 2H), 2.36-2.31(t, 2H), 1.93-1.86(m, 2H), 1.70-1.31(m, 6H).

Workup

  1. customto precipitate a gum
  2. customThis residue was triturated with ethyl ether

Sources & evidence

ORD record
ord-bdeed3e85cb44c63b9ab48a5c0748b1a
Source dataset
uspto-grants-1993_01
Patent number
US05179117

Reaction notes

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