Methanol → HCID 59314400, compound

HRID 1047925Notes

Reaction equation

HRID 1047925 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16](=[O:28])[C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[O:24][CH2:25][C:26]#[N:27])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5])C.O1CCOCC1.CO.O>CO.C(Cl)Cl>[C:26]([CH2:25][O:24][C:18]1[C:19]([CH3:23])=[CH:20][CH:21]=[CH:22][C:17]=1[C:16]([NH:15][C:6]1([C:4]([OH:5])=[O:3])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:28])#[N:27]

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 312751,4-DioxaneHCID 59314118HCID 59314118, compound

Product 1

HCID 59314400HCID 59314400, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

A 100 mL flask containing 2-(2-cyanomethoxy-3-methyl-benzoylamino)-indan-2-carboxylic acid ethyl ester (330, 0.25 g, 0.66 mmol) is charged with 1,4-dioxane (2 mL) and MeOH (2 mL). A stirring bar is added and stirring is initiated. After dissolution, water (1 mL) is added followed by the LiOH monohydrate (71 mg, 1.67 mmol). After 18 h, tlc analysis (silica, 5% MeOH/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%, ˜8 mL). The contents of the flask are poured into a separatory funnel which contains EtOAc (25 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), and then dried over MgSO4, filtered and concentrated by pumping to constant weight to give white solid (0.23 g, 99%).

Workup

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

Sources & evidence

ORD record
ord-a180b5e864a144c8922581dadabc040a
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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