Hydrochloric Acid → HCID 118207084, compound

HRID 528506Notes

Reaction equation

HRID 528506 reaction equation
[CH3:1][CH:2]1[C:10]2[CH:9]=[C:8]3[O:11][CH2:12][O:13][C:7]3=[CH:6][C:5]=2[C:4](=[O:14])[N:3]1[CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][CH2:18]1.C(O)C.[ClH:33]>C(OCC)(=O)C>[ClH:33].[CH3:1][CH:2]1[C:10]2[CH:9]=[C:8]3[O:11][CH2:12][O:13][C:7]3=[CH:6][C:5]=2[C:4](=[O:14])[N:3]1[CH2:15][CH2:16][CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 90064484HCID 90064484, compound

Product 1

HCID 118207084HCID 118207084, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a reaction vessel, 5 g (0.012 mol) compound XIII, 30 ml ethanol and 100 ml 10% solution of hydrogen chloride in ethyl acetate were added, the reaction was kept at room temperature for 1-1.5 h, filtered, the filter cake was washed with ethyl acetate, dried, and 3.4 g compound II-3 was obtained, with yield of 81%. 1H NMR (D2O): δ 1.24 (d, 3H, J=7.0 Hz), 1.44-1.58 (m, 5H), 1.98 (m, 2H), 2.96 (m, 2H), 3.21-3.25 (m, 1H), 3.44 (d, 2H, J=12.4 Hz), 3.64-3.72 (m, 1H), 4.34 (q, 1H, J=6.6 Hz), 5.94 (s, 2H), 6.72 (s, 1H), 6.79 (s, 1H); MS (ESI): m/z 303 [M+H]+.

Workup

  1. filtrationfiltered
  2. washthe filter cake was washed with ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-312ec601115a4813969d8ae825c203e6
Source dataset
uspto-grants-2016_05
Patent number
US09346818B2

Reaction notes

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