Hydrochloric Acid → HCID 178511815, compound

HRID 1023874Notes

Reaction equation

HRID 1023874 reaction equation
C([C@@H]1C(OC)=[N:8][C@@H:7]([CH2:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]2[N:21]=[CH:22][N:23](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:24]=2)[C:6]([O:44]C)=N1)(C)C.Cl.[OH:47][Li:48].O>C(O)C>[NH:23]1[CH:24]=[C:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH2:13][CH2:12][C@H:7]([NH2:8])[C:6]([O-:44])=[O:47])[N:21]=[CH:22]1.[Li+:48]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 67207459HCID 67207459, compound

Product 1

HCID 178511815HCID 178511815, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

(2R,5S)-2-isopropyl-3,6-dimethoxy-5-(2-(1-trityl-1H-imidazol-4-yl)phenethyl)-2,5-dihydropyrazine (87 mg, 0.146 mmol) was dissolved in ethanol (3 mL) and concentrated HCl (few drops) was added. The mixture was heated at 70° C. for 2 h and concentrated. The residue was taken up in MeOH/water (3:1, 4 mL) and LiOH.H2O (6 mg, 0.146 mmol) was added. The mixture was stirred at room temperature for 18 h and concentrated. The crude product was washed with dichloromethane, hexanes, suspended in methanol and filtered. The filtrate was concentrated to afford the desired product (30 mg, 0.120 mmol, 83%) as a white solid. 1H NMR (MeOH-d4): 0.84-1.00 (m, 2H), 1.86-1.94 (m, 1H), 2.77-2.85 (m, 1H), 4.26-4.28 (m, 1H), 7.10-7.19 (m, 3H), 7.23-7.28 (m, 1H), 7.41 (d, 1H, J=2.8 Hz), 7.64 (s, 1H).

Workup

  1. concentrationconcentrated
  2. concentrationconcentrated
  3. washThe crude product was washed with dichloromethane, hexanes
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-49e0953878fe411db9ff92c389851d31
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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