Hydrochloric Acid → HCID 69584947, compound

HRID 2212449Notes

Reaction equation

HRID 2212449 reaction equation
C([O:5][C:6]([CH2:8][O:9][C:10](=[O:41])[C:11]([NH:32][NH:33]C(OC(C)(C)C)=O)([CH3:31])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:15]([O:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:14]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O.Cl>C(Cl)Cl.O1CCOCC1>[C:6]([CH2:8][O:9][C:10](=[O:41])[C:11]([NH:32][NH2:33])([CH3:31])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:15]([O:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH:14]=1)([OH:7])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 69584969HCID 69584969, compound

Product 1

HCID 69584947HCID 69584947, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Compound 155 was dissolved in 2 mL CH2Cl2 and treated with 1 mL trifluoroacetic acid at 0° C. The resulting mixture was allowed to warm to room temperature and stirred for 1 h. The reaction mixture was cooled to 0° C. again and a solution (1 mL) of 4 N HCl in dioxane was added. After stirring at room temperature for 2 h, the solvent was removed in vacuo. The crude residue was purified by reverse phase LC/MS to afford 103 mg (24% overall yield) of the title compound. 1H-NMR (400 MHz, CD3OD): δ 7.14–7.22 (m, 3H), 4.49–4.69 (Abq, J=62.8, 14.8, 2H), 4.24–4.29 (m, 4H), 3.03–3.13 (q, J=13.6 Hz), 1.33 (t, J=6.0 Hz, 6H). MS (ESI) m/z 429.2 (M+H+).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C. again
  2. stirringAfter stirring at room temperature for 2 h
  3. customthe solvent was removed in vacuo
  4. customThe crude residue was purified by reverse phase LC/MS
  5. customto afford

Sources & evidence

ORD record
ord-52a803844bc04d92978d06e334de8133
Source dataset
uspto-grants-2006_09
Patent number
US07101912B2

Reaction notes

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