Ethanol → HCID 11442092, compound

HRID 2118222Notes

Reaction equation

HRID 2118222 reaction equation
[N+](C1C=C[C:7]([O:8][C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15](/[C:18](/[C:28]3[CH:33]=[CH:32][C:31](/[CH:34]=[CH:35]/[C:36]([O:38]C(C)(C)C)=[O:37])=[CH:30][CH:29]=3)=[C:19](\[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)/[CH2:20][CH3:21])=[CH:14][CH:13]=2)=[O:10])=[CH:6]C=1)([O-])=O.CCO.CCN(CC)CC>C(Cl)Cl>[CH2:7]([O:8][C:9]([O:11][C:12]1[CH:13]=[CH:14][C:15](/[C:18](/[C:28]2[CH:33]=[CH:32][C:31](/[CH:34]=[CH:35]/[C:36]([OH:38])=[O:37])=[CH:30][CH:29]=2)=[C:19](\[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)/[CH2:20][CH3:21])=[CH:16][CH:17]=1)=[O:10])[CH3:6]

Participants

5

Reactant 3

HCID 702EthanolHCID 8471TriethylamineHCID 58877664HCID 58877664, compound

Product 1

HCID 11442092HCID 11442092, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 38 (0.050 g, 0.084 mmol) in CH2Cl2 (2 mL) was added EtOH (0.050 g, 1.08 mmol) and Et3N (0.016 g, 0.16 mmol). The mixture was stirred at ambient temperature for 18 h, diluted with CH2Cl2, washed with water and 0.1 N hydrochloric acid, dried (Na2SO4), and concentrated. The residue was separated by preparative RP-HPLC (C-18 Luna column, 85% MeCN/H2O/0.1% TFA) and the corresponding fractions were concentrated. The residue was dissolved in CH2Cl2 (0.3 mL) and cooled to 0° C. TFA (0.3 mL) was added and the mixture stirred at 0° C. for 1 h. The solvent was evaporated and co-evaporated with CH2Cl2 (2×10 mL) and the residue crystallized from a small amount of EtOAC to provide 37 (0.010 g) as an off-white solid; mp 135-136° C.; 1HNMR (DMSO-d6): δ 0.85 (t, J=7.2 Hz, 3H), 1.21 (t, J=7.2 Hz, 3H), 2.39 (q, J=7.2 Hz, 2H), 4.15 (q, J=7.2 Hz, 2H), 6.5 (d, J=16 Hz, 1H), 6.85 (d, J=9 Hz, 2H), 6.89 (d, J=9 Hz, 2H), 7.08-7.22 (m, 5H), 7.24 (d, J=7.9 Hz, 2H), 7.58 (d, J=16 Hz, 1H), 7.69 (d, J=7.9 Hz, 2H), 12.45 (br s, 1H); MS, m/z 465 (M+Na)+; Anal. calculated for C28H26O5.0.13H2O: C, 75.60; H, 5.95; Found: C, 75.61; H, 5.93.

Workup

  1. washwashed with water and 0.1 N hydrochloric acid
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe residue was separated by preparative RP-HPLC (C-18 Luna column, 85% MeCN/H2O/0.1% TFA)
  5. concentrationthe corresponding fractions were concentrated
  6. dissolutionThe residue was dissolved in CH2Cl2 (0.3 mL)
  7. temperaturecooled to 0° C
  8. additionTFA (0.3 mL) was added
  9. stirringthe mixture stirred at 0° C. for 1 h
  10. customThe solvent was evaporated
  11. customthe residue crystallized from a small amount of EtOAC

Sources & evidence

ORD record
ord-0555d85f94284658b6d855770c9af159
Source dataset
uspto-grants-2008_10
Patent number
US07442833B2

Reaction notes

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