Methanol → HCID 15341837, compound

HRID 1033653Notes

Reaction equation

HRID 1033653 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:37][CH:38]=[CH2:39])=[C:5]([CH:27]=[CH:28][C:29]=1[C:30]([N:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1)=[O:31])[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[C:12]([CH2:24][CH2:25][CH3:26])=[C:13]([CH:21]=[CH:22][CH:23]=1)[O:14][CH2:15][C:16]([O:18]CC)=[O:17].[OH-].[Li+].CO>C(OCC)(=O)C.CCCCCC>[CH3:1][O:2][C:3]1[C:4]([CH2:37][CH:38]=[CH2:39])=[C:5]([CH:27]=[CH:28][C:29]=1[C:30]([N:32]1[CH2:33][CH2:34][CH2:35][CH2:36]1)=[O:31])[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[C:12]([CH2:24][CH2:25][CH3:26])=[C:13]([CH:21]=[CH:22][CH:23]=1)[O:14][CH2:15][C:16]([OH:18])=[O:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 15341836HCID 15341836, compound

Product 1

HCID 15341837HCID 15341837, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The compound of Example 58 (95 mg, 0.176 mmol) and 352 μl (0.352 mmol) of 1M lithium hydroxide were added to 2.0 ml of methanol. The reaction mixture was stirred at room temperature for 4 hours and the solvent was removed under vacuum. Water (5.0 ml) was added to the residue, and the mixture was acidified with 10% hydrochloric acid then extracted three times with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate and filtered. The solvent was removed under vacuum to give a gum. Chromatography of the gum on silica gel with 50/50 ethyl acetate/hexane as eluant followed by drying under vacuum overnight gave the product.

Workup

  1. customthe solvent was removed under vacuum
  2. additionWater (5.0 ml) was added to the residue
  3. extractionthen extracted three times with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed under vacuum
  7. customto give a gum
  8. customby drying under vacuum overnight
  9. customgave the product

Sources & evidence

ORD record
ord-a605c055b2d2436199dadcb0fc2d18ee
Source dataset
uspto-grants-1994_05
Patent number
US05310951

Reaction notes

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