Hydrochloric Acid → Coelenterazine

HRID 1616965Notes

Reaction equation

HRID 1616965 reaction equation
C(OC(OCC)C(=O)CC1C=CC(C)=CC=1)C.[CH:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]2[NH:34][C:33]([C:35]3[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=3)=[CH:32][N:31]3[C:26]=2[N:27]=[C:28]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=2)[C:29]3=[O:30])=[CH:20][CH:19]=1.Cl>O1CCOCC1.O>[CH:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]2[C:26]3[N:31]([CH:32]=[C:33]([C:35]4[CH:36]=[CH:37][C:38]([OH:41])=[CH:39][CH:40]=4)[N:34]=2)[C:29]([OH:30])=[C:28]([CH2:42][C:43]2[CH:48]=[CH:47][C:46]([OH:49])=[CH:45][CH:44]=2)[N:27]=3)=[CH:20][CH:19]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 49766391HCID 49766391, compoundHCID 1785156498-benzyl-6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-7H-imidazo[1,2-a]pyrazin-3-one

Product 1

HCID 135445694CoelenterazineYield 60.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, 1,1-diethoxy-3-(4-methylphenyl)propan-2-one (33) (216 mg, 914 μmol) was dissolved in 1,4-dioxane (2 mL) and water (0.4 mL). To this was added coelenteramine (196 mg, 707 μmol) and, after cooling to 0° C., conc. hydrochloric acid (0.20 mL) was further added thereto, and then stirred overnight (14 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→20/1). The solid obtained was further reprecipitated (n-hexane/acetone) to give me-coelenterazine (34, me-CTZ) as a yellow powder (180 mg, 427 μmol, 60.4%).

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→20/1)
  4. customThe solid obtained
  5. customwas further reprecipitated (n-hexane/acetone)

Sources & evidence

ORD record
ord-88b022823b4c4a25a8e9129e6deffdd5
Source dataset
uspto-grants-2014_07
Patent number
US08765921B2

Reaction notes

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