Hydrochloric Acid → HCID 118057354, compound

HRID 528504Notes

Reaction equation

HRID 528504 reaction equation
[O:1]=[C:2]1[C:10]2[CH:9]=[C:8]3[O:11][CH2:12][O:13][C:7]3=[CH:6][C:5]=2[CH2:4][N:3]1[CH2:14][CH2:15][CH:16]1[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]1.[ClH:29]>C(OCC)(=O)C>[ClH:29].[NH:19]1[CH2:20][CH2:21][CH:16]([CH2:15][CH2:14][N:3]2[C:2](=[O:1])[C:10]3[CH:9]=[C:8]4[O:11][CH2:12][O:13][C:7]4=[CH:6][C:5]=3[CH2:4]2)[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 90064483HCID 90064483, compound

Product 1

HCID 118057354HCID 118057354, compoundYield 84.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a reaction vessel, 15 g (0.039 mol) compound XII and 300 ml 10% solution of hydrogen chloride in ethyl acetate were added, the reaction mixture was kept at room temperature for 30 min until the reaction was complete, concentrated to dry under reduced pressure, recrystallized with the mixed solution of ethanol and ethyl acetate, and 10.5 g compound II-2 was obtained, with yield of 84.3%. 1H NMR (D2O): δ 1.38-1.49 (m, 2H), 1.59-1.61 (m, 3H), 1.98 (d, 2H, J=13.5 Hz), 2.91-2.98 (m, 2H), 3.42 (d, 2H, J=12.8 Hz), 3.49 (t, 2H, J=7.0 Hz), 4.13 (s, 2H), 5.97 (s, 2H), 6.72 (s, 1H), 6.76 (s, 1H); MS (ESI): m/z 289 [M−Cl]+.

Workup

  1. concentrationconcentrated
  2. customto dry under reduced pressure
  3. customrecrystallized with the mixed solution of ethanol and ethyl acetate

Sources & evidence

ORD record
ord-88c348801e8e4fdaa4980602580c252b
Source dataset
uspto-grants-2016_05
Patent number
US09346818B2

Reaction notes

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