Hydrochloric Acid → Coelenterazine

HRID 1616967Notes

Reaction equation

HRID 1616967 reaction equation
C(OC(OCC)C(=O)CC1C=CC(CC)=CC=1)C.[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]2[NH:35][C:34]([C:36]3[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=3)=[CH:33][N:32]3[C:27]=2[N:28]=[C:29]([CH2:43][C:44]2[CH:49]=[CH:48][C:47]([OH:50])=[CH:46][CH:45]=2)[C:30]3=[O:31])=[CH:21][CH:20]=1.Cl>O1CCOCC1.O>[CH:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]2[C:27]3[N:32]([CH:33]=[C:34]([C:36]4[CH:37]=[CH:38][C:39]([OH:42])=[CH:40][CH:41]=4)[N:35]=2)[C:30]([OH:31])=[C:29]([CH2:43][C:44]2[CH:49]=[CH:48][C:47]([OH:50])=[CH:46][CH:45]=2)[N:28]=3)=[CH:21][CH:20]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 66724860HCID 66724860, compoundHCID 1785156498-benzyl-6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-7H-imidazo[1,2-a]pyrazin-3-one

Product 1

HCID 135445694CoelenterazineYield 64.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, 1,1-diethoxy-3-(4-ethylphenyl)propan-2-one (43) (301 mg, 1.20 mmol) was dissolved in 1,4-dioxane (2 mL) and water (0.4 mL). To this was added coelenteramine (238 mg, 858 μmol) and, after cooling to 0° C., conc. hydrochloric acid (0.20 mL) was further added thereto, and then stirred overnight (17 hours) at 100° C. After cooling to room temperature, the mixture was concentrated under reduced pressure and the residue was purified by silica gel flash chromatography in an argon flow (n-hexane/ethyl acetate═1/2→ethyl acetate→ethyl acetate/methanol═50/1→10/1). The solid obtained was further reprecipitated (n-hexane/acetone) to give et-coelenterazine (44, et-CTZ) as a yellow powder (240 mg, 551 μmol, 64.2%).

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel flash chromatography in an argon flow (n-hexane/ethyl acetate═1/2→ethyl acetate→ethyl acetate/methanol═50/1→10/1)
  4. customThe solid obtained
  5. customwas further reprecipitated (n-hexane/acetone)

Sources & evidence

ORD record
ord-45a2adbe299e4aeab975a9423cc318e9
Source dataset
uspto-grants-2014_07
Patent number
US08765921B2

Reaction notes

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