Methanol → HCID 66815646, compound

HRID 2367923Notes

Reaction equation

HRID 2367923 reaction equation
[C:1]([O:5][C:6](=[O:27])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[C:20]([C:23]([O:25]C)=[O:24])[CH:19]=[CH:18]2)([CH3:4])([CH3:3])[CH3:2].CO>C(OCC)(=O)C.CCCCCC.C(O)(=O)C>[C:1]([O:5][C:6](=[O:27])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:22]=1[N:21]=[C:20]([C:23]([OH:25])=[O:24])[CH:19]=[CH:18]2)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 887MethanolHCID 67773395HCID 67773395, compound

Product 1

HCID 66815646HCID 66815646, compound

Reagents, catalysts & solvents 1

HCID 21901998Ethyl acetate hexane acetic acidSolvent

Procedure

To a solution of compound 1 (540 mg, 1.45 mmol, 1 eq.) in MeOH (3 mL) NaOH (116 mg, 2.9 mmol, 2 eq.) was added as, a concentrated aqueous solution, and the mixture was stirred at room temperature. The reaction was monitored by TLC (ethyl acetate/hexane/acetic acid, 1:1:0.01). Upon completion the volatiles were removed in vacuo and ethyl acetate added. The solution was washed with NaH2PO4 buffer (pH 5, 1M) and brine, dried over Na2SO4, and concentrated in vacuo to give 446 mg of crude 2, which was used directly in the next step. MS m/z 360 [M−H]+

Workup

  1. customUpon completion the volatiles were removed in vacuo and ethyl acetate
  2. additionadded
  3. washThe solution was washed with NaH2PO4 buffer (pH 5, 1M) and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto give 446 mg of crude 2, which

Sources & evidence

ORD record
ord-8a3ab6d0e0ef45a09927719a63c9fab4
Source dataset
uspto-grants-2014_04
Patent number
US08703700B2

Reaction notes

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