HCID 68903266, compound → HCID 178442324, compound

HRID 2110583Notes

Reaction equation

HRID 2110583 reaction equation
[CH2:1]([O:8][N:9]1[C:13]2([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:14]3[C:19]([C:20](=[O:22])[CH:21]=[C:12]2[O:11]C1C(C)C)=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>O1CCCC1.Cl>[CH2:1]([O:8][NH:9][C:13]1([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:20](=[O:22])[CH:21]=[C:12]1[OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 68903266HCID 68903266, compound

Product 1

HCID 178442324HCID 178442324, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of Example 17E (1.36 g, 3.35 mmol) in tetrahydrofuran(12 mL) and 2N HCl (6 mL) was stirred at 25° C. for 2 hours. The mixture was concentrated in vacuo and the resulting oil was triturated with ethyl acetate. The white hydrochloride salt was filtered, suspended in ethyl acetate, and basified to pH 10 with 1N NaHCO3. The ethyl acetate layer was dried (Na2SO4), filtered, and concentrated in vacuo to afforded the title compound as an amber oil (1 g, 84.8%) and used for the next step without further purification. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.34-0.51 (m, 1H), 0.63 (d, J=6.62 Hz, 3H), 0.69 (d, J=6.62 Hz, 3H), 0.72-0.89 (m, 1H), 0.92-1.09 (m, 1H), 1.16-1.31 (m, 1H), 1.46-1.77 (m, 2H), 4.23 (d, 1H), 4.30-4.40 (m, 1H), 5.71 (s, 1H), 6.84-6.95 (m, 2H), 7.06 (s, 1H), 7.19 (q, J=3.55 Hz, 3H), 7.45 (t, J=6.99 Hz, 1H), 7.61 (t, J=7.17 Hz, 1H), 7.84 (d, J=7.72 Hz, 1H), 7.87 (d, 1H), 11.78 (br.s, 1H); MS (ESI) m/z 352.0 (M+H)+.

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe resulting oil was triturated with ethyl acetate
  3. filtrationThe white hydrochloride salt was filtered
  4. dry with materialThe ethyl acetate layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eceb8b5bfe174987a3a460947a58e39b
Source dataset
uspto-grants-2009_04
Patent number
US07517876B2

Reaction notes

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