Sodium Hydroxide → HCID 10344629, compound

HRID 1825324Notes

Reaction equation

HRID 1825324 reaction equation
[C:1]([C@H:4]([CH2:31][CH2:32][O:33][CH3:34])[CH2:5][C:6]1([C:11]([NH:13][C@@H:14]([CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[CH2:15][C:16]([O:18]CC)=[O:17])=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1)([OH:3])=[O:2].[OH-].[Na+]>O1CCOCC1>[C:1]([C@H:4]([CH2:31][CH2:32][O:33][CH3:34])[CH2:5][C:6]1([C:11]([NH:13][C@@H:14]([CH2:21][CH2:22][O:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[CH2:15][C:16]([OH:18])=[O:17])=[O:12])[CH2:10][CH2:9][CH2:8][CH2:7]1)([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10481018HCID 10481018, compound

Product 1

HCID 10344629HCID 10344629, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of the ethyl ester from example 47 (100 mg, 0.20 mmol) and 2N sodium hydroxide solution (2 ml) in dioxan (4 ml) was stirred at 50° C. for 3 hours, then concentrated under reduced pressure. The residue was suspended in 2N hydrochloric acid (2 ml), extracted with ethyl acetate (3×20 ml), and the combined organic solutions dried (MgSO4) and evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:methanol:acetic acid (90:10:0 to 90:10:1) to afford the title compound as a colourless oil, 50 mg; 1H NMR (CDCl3, 400 MHz) δ: 1.45–1.78 (m, 8H), 1.85–2.19 (m, 6H), 2.56 (m, 1H), 2.62 (m, 2H), 3.37 (m, 4H), 3.46 (m, 1H), 4.00 (t, 2H), 4.62 (m, 1H), 6.64 (d, 1H), 6.81 (d, 2H), 7.22 (d, 2H); LRMS: m/z (ES−) 468 [M-H]−.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionextracted with ethyl acetate (3×20 ml)
  3. dry with materialthe combined organic solutions dried (MgSO4)
  4. customevaporated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel using an elution gradient of ethyl acetate:methanol:acetic acid (90:10:0 to 90:10:1)

Sources & evidence

ORD record
ord-22623a2f305f4202a620ea5e281c9c93
Source dataset
uspto-grants-2006_05
Patent number
US07045653B2

Reaction notes

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