HCID 86660872, compound → HCID 66656204, compound

HRID 1035180Notes

Reaction equation

HRID 1035180 reaction equation
C(O)=O.[CH3:4][N:5]([CH2:7][C:8]1[CH:25]=[CH:24][C:11]([O:12][CH:13]2[CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14]2)=[C:10]([CH3:26])[CH:9]=1)[CH3:6]>Cl.CO>[NH:15]1[CH2:14][CH:13]([O:12][C:11]2[CH:24]=[CH:25][C:8]([CH2:7][N:5]([CH3:6])[CH3:4])=[CH:9][C:10]=2[CH3:26])[CH2:16]1

Participants

4

Reactant 1

HCID 86660872HCID 86660872, compound

Product 1

HCID 66656204HCID 66656204, compoundYield 78.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

Intermediate 16A (1.9 g, 5.93 mmol) was dissolved in a 4.0 M solution of HCl in MeOH (30 mL) and the reaction mixture was stirred at RT overnight. The mixture was concentrated and the residue was dissolved in water. The aqueous solution was basified to pH=10 with aqueous NaOH (1.0 M) and then extracted with DCM (4×30 mL). The combined organic phases were filtered through a phase separator and the solvent was removed by evaporation. There was obtained 1.02 g (78%) of 16B as a colorless oil. 1H NMR (500 MHz, CDCl3): δ 2.21 (s, 6H), 2.33 (s, 3H), 3.30 (s, 2H), 3.73-3.84 (m, 2H), 3.85-3.96 (m, 2H), 4.91-5.03 (m, 1H), 6.52 (d, 1H), 6.58 (s, 1H), 7.11 (d, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with DCM (4×30 mL)
  4. filtrationThe combined organic phases were filtered through a phase separator
  5. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-914cfa2e04b647d39c9a2fb10cf28143
Source dataset
uspto-grants-2013_10
Patent number
US08546375B2

Reaction notes

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