Water → HCID 131717711, compound

HRID 1646276Notes

Reaction equation

HRID 1646276 reaction equation
[C:1]12([C:11](Cl)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.Br.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:24]=[C:25]([S:36][CH2:37][CH2:38][CH2:39][C:40]([NH:42][C@H:43]([C:49]([O:51][CH3:52])=[O:50])[CH2:44][CH2:45][CH2:46][CH2:47][NH2:48])=[O:41])[NH:26][C:27]=2[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[CH:19][CH:18]=1.C(N(CC)CC)C.O>C(Cl)Cl>[C:1]12([C:11]([NH:48][CH2:47][CH2:46][CH2:45][CH2:44][C@@H:43]([C:49]([O:51][CH3:52])=[O:50])[NH:42][C:40](=[O:41])[CH2:39][CH2:38][CH2:37][S:36][C:25]3[NH:26][C:27]([C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)=[C:23]([C:20]4[CH:21]=[CH:22][C:17]([O:16][CH3:15])=[CH:18][CH:19]=4)[N:24]=3)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 131717708HCID 131717708, compound

Product 1

HCID 131717711HCID 131717711, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-adamantanecarbonyl chloride (0.159 g, 0.000804 mol) in methylene chloride (2 ml) was added to a mixture of N2-[4-[4,5-bis(4-methoxyphenyl)-1H-imidazol-2-ylthio]-1-oxobutyl]-L-lysine, methyl ester hydrobromide (0.5 g, 0.000804 mol), triethyl amine (0.24 g, 0.0024 mol) and methylene chloride (20 ml) at ambient temperature under a nitrogen atmosphere. The reaction mixture was stirred for 2 hours, poured into water and extracted with ethyl acetate. The combined organic layer was washed with saturated aqueous ammonium chloride, water, brine, dried over magnesium sulfate and concentrated to give a foam. The foam was purified by flash chromatography on silica gel (50 ml) eluting ethyl acetate to give the title compound (0.4 g, 0.00057 mol, 71% yield) as a white foam, mp 98°-104°. 1H NMR (DMSO-d6) δ8.22(d, 1H), 7.35-7.25(m, 5H), 6.87(d, 4H), 4.2-4.12(m, 1H), 3.75(s, 6H), 3.57(s, 3H), 3.1-2.93(m, 4H), 2.27(t, 2H), 1.97-1.5(m, 19H), 1.37-1.17(m, 4H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layer was washed with saturated aqueous ammonium chloride, water, brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give a foam
  6. customThe foam was purified by flash chromatography on silica gel (50 ml)
  7. washeluting ethyl acetate

Sources & evidence

ORD record
ord-32bc47cc35f8487098eafafe29de2d57
Source dataset
uspto-grants-1993_01
Patent number
US05179117

Reaction notes

Loading…