Methanol → HCID 86759659, compound

HRID 1815978Notes

Reaction equation

HRID 1815978 reaction equation
Br[CH:2]1[CH2:28][O:27][C:5]2=[CH:6][CH:7]=[C:8]3[C:12]([N:11]([CH2:13][C@@H:14]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH3:15])[N:10]=[CH:9]3)=[C:4]2[CH:3]1[OH:29].[OH-:30].[Na+].[CH3:32]O>O1CCCC1>[OH:30][CH:2]1[CH2:28][O:27][C:5]2=[CH:6][CH:7]=[C:8]3[C:12]([N:11]([CH2:13][C@@H:14]([NH:16][C:17](=[O:26])[O:18][CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[CH3:15])[N:10]=[CH:9]3)=[C:4]2[CH:3]1[O:29][CH3:32]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 86759658HCID 86759658, compound

Product 1

HCID 86759659HCID 86759659, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 11, Step A (0.46 g, 1.12 mmol) in tetrahydrofuran (50 mL) was added 2 N sodium hydroxide (6 mL). After stirring for 10 min, methanol (10 mL) was added and the mixture stirred for 1 h followed by evaporation to a residue, which was mixed with water (50 mL) and extracted with ethyl acetate (3×50 mL). The combined extracts were dried over magnesium sulfate, filtered and evaporated to a residue, which was purified by chromatography (silica, 20 to 35% ethyl acetate in hexane) to give an oil (0.45 g): LC/MS (+APCI) m/z 378 (M+H).

Workup

  1. stirringthe mixture stirred for 1 h
  2. customfollowed by evaporation to a residue, which
  3. additionwas mixed with water (50 mL)
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated to a residue, which
  8. customwas purified by chromatography (silica, 20 to 35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-05ded152655a4d0bbc6f8d0196aaa50c
Source dataset
uspto-grants-2005_04
Patent number
US06881749B2

Reaction notes

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