Methanol → HCID 59314246, compound

HRID 1047826Notes

Reaction equation

HRID 1047826 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[C:26]3[O:25][C:24]([CH3:27])=[CH:23][C:22]=3[CH:21]=[CH:20][CH:19]=2)=[O:17])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.O1CCOCC1.CO.[Li+].[OH-]>CC(O)C.C(Cl)Cl.O>[CH3:27][C:24]1[O:25][C:26]2[C:18]([C:16]([NH:15][C:6]3([C:4]([OH:5])=[O:3])[CH2:14][C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[CH2:7]3)=[O:17])=[CH:19][CH:20]=[CH:21][C:22]=2[CH:23]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 59314316HCID 59314316, compound

Product 1

HCID 59314246HCID 59314246, compoundYield 100.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21966342Isopropanol methylene chlorideSolvent

Procedure

A 50 mL flask containing the 2-[(2-methylbenzofuran-7-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (0.40 g, 1.10 mmol) is charged with 1,4-dioxane (4 mL) and MeOH (4 mL). A stirring bar is added and stirring is initiated. After dissolution, water (2 mL) is added followed by the LiOH (115 mg, 2.75 mmol). After 18 h, tlc analysis (silica, 5% i-PrOH/DCM) indicates that the starting material is completely consumed. The pH of the reaction mixture is carefully adjusted to pH 2 by slowly adding dilute aqueous HCl (3%, ˜12 mL). The contents of the flask are poured into a reparatory funnel containing EtOAc (30 mL). The layers are separated. The aqueous layer is extracted with EtOAc (20 mL). The combined organic extracts are washed with water (20 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated by vacuum to constant weight to give 0.37 g of white solid.

Workup

  1. additionA stirring bar is added
  2. additionis added
  3. customis completely consumed
  4. additionby slowly adding dilute aqueous HCl (3%, ˜12 mL)
  5. additionThe contents of the flask are poured into a reparatory funnel
  6. additioncontaining EtOAc (30 mL)
  7. customThe layers are separated
  8. extractionThe aqueous layer is extracted with EtOAc (20 mL)
  9. washThe combined organic extracts are washed with water (20 mL) and brine (20 mL)
  10. dry with materialdried over MgSO4
  11. filtrationfiltered
  12. concentrationconcentrated by vacuum to constant weight

Sources & evidence

ORD record
ord-40f9ada0e1184581b435ebea5b3935b6
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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