Hydrochloric Acid → HCID 178515647, compound

HRID 873034Notes

Reaction equation

HRID 873034 reaction equation
[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][C:16](=O)[CH:17]([O:21]CC)OCC)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.[NH2:25][C:26]1[C:35]([CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)=[N:34][C:33]2[C:32]3[CH:43]=[CH:44][C:45]([OH:47])=[CH:46][C:31]=3[CH:30]=[CH:29][C:28]=2[N:27]=1.Cl>C(O)C.O>[CH:40]1[CH:39]=[CH:38][C:37]([CH2:36][C:35]2[NH:34][C:33]3[C:32]4[CH:43]=[CH:44][C:45]([OH:47])=[CH:46][C:31]=4[CH:30]=[CH:29][C:28]=3[N:27]3[C:26]=2[N:25]=[C:16]([CH2:15][C:12]2[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=2)[C:17]3=[O:21])=[CH:42][CH:41]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 112796253-(4-(Tert-butyldimethylsilyloxy)phenyl)-1,1-diethoxypropan-2-oneHCID 178508157HCID 178508157, compound

Product 1

HCID 178515647HCID 178515647, compoundYield 13.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Under an argon atmosphere, to a solution of 3-(4-(tert-butyldimethylsilyloxy)phenyl)-1,1-diethoxypropan-2-one (15) (101 mg, 286 μmol) in ethanol (2 mL) and water (0.4 mL) was added 3-amino-2-benzylbenzo[f]quinoxalin-8-ol (14) (55.5 mg, 184 μmol). After cooling to 0° C., to the mixture was further added conc. hydrochloric acid (0.20 mL). The mixture was heated to 80° C. and stirred overnight (18 hours). After cooling to room temperature and concentration under reduced pressure, the residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=1/1→1/2→ethyl acetate alone) in an argon flow to give v-coelenterazine (2, v-CTZ) (10.9 mg, 24.4 μmol, 13.2%) as ocherous powders. TLC Rf=0.50 (n-hexane/ethyl acetate=1/1); 1H NMR (500 MHz, CD3OD) δ 4.08 (s, 2H), 4.51 (s, 2H), 6.69-6.72 (AA′BB′, 2H), 7.17-7.24 (m, 5H), 7.29 (t, 2H, J=7.5 Hz), 7.43 (d, 2H, J=7.5 Hz), 7.63 (d, 1H, J=8.5 Hz), 8.40 (br, 1H), 9.26 (br, 1H).

Workup

  1. temperatureThe mixture was heated to 80° C.
  2. temperatureAfter cooling to room temperature
  3. concentrationconcentration under reduced pressure
  4. customthe residue was purified by silica gel flash column chromatography (n-hexane/ethyl acetate=1/1→1/2→ethyl acetate alone) in an argon flow

Sources & evidence

ORD record
ord-2eb3eaefb5b94417ae7d2dcb9b868945
Source dataset
uspto-grants-2015_03
Patent number
US08975403B2

Reaction notes

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