Methanol → 2-[(Benzo[b]thiophene-3-carbonyl)-amino]-indane-2-carboxylic acid

HRID 1047816Notes

Reaction equation

HRID 1047816 reaction equation
C([O:3][C:4]([C:6]1([NH:15][C:16]([C:18]2[C:19]3[CH:26]=[CH:25][CH:24]=[CH:23][C:20]=3[S:21][CH:22]=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-]>O>[S:21]1[CH:22]=[C:18]([C:16]([NH:15][C:6]2([C:4]([OH:5])=[O:3])[CH2:14][C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[CH2:7]2)=[O:17])[C:19]2[CH:26]=[CH:25][CH:24]=[CH:23][C:20]1=2

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 312751,4-DioxaneHCID 593143652-[(Benzo[b]thiophene-3-carbonyl)-amino]-indane-2-carboxylic acid ethyl ester

Product 1

HCID 593142342-[(Benzo[b]thiophene-3-carbonyl)-amino]-indane-2-carboxylic acidYield 121.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 50 mL flask containing the 2-[(benzo[b]thiophene-3-carbonyl)-amino]-indan-2-carboxylic acid ethyl ester (182, 0.40 g, 1.10 mmol) is charged with 1,4-dioxane (10 mL) and MeOH 10 mL). A stirring bar is added and stirring is initiated. After dissolution, water (5.0 mL) is added followed by the LiOH (115 mg, 2.74 mmol). After 18 h, tlc analysis (silica, 50% EtOAc/heptanes) indicates that the starting material is completely consumed. Dilute aqueous HCl (3%, ˜15 mL) and EtOAc (25 mL) are added to the reaction flask. After stirring for 10 min, the contents of the flask are poured into a reparatory funnel. The layers are separated. The aqueous layer is extracted with EtOAc (30 mL). The combined organic extracts are washed with water (20 mL) and brine (20 mL), dried over MgSO4, filtered and concentrated. Pumping to constant weight gives 450 mg of a dry white powder.

Workup

  1. additionA stirring bar is added
  2. additionis added
  3. customis completely consumed
  4. additionDilute aqueous HCl (3%, ˜15 mL) and EtOAc (25 mL) are added to the reaction flask
  5. stirringAfter stirring for 10 min
  6. additionthe contents of the flask are poured into a reparatory funnel
  7. customThe layers are separated
  8. extractionThe aqueous layer is extracted with EtOAc (30 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

Sources & evidence

ORD record
ord-0ab92d5e713d4192a12d76319ec13717
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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