Lithium Hydroxide → (3R)-3-[(2-chloro-benzoyl)amino]-2,3-dihydro-1H-indene-5-carboxylic acid
Reaction equation
[Li+].[OH-].C[O:4][C:5]([C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[CH2:12][CH2:11][C@H:10]2[NH:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24])=[O:6]>CO.O>[Cl:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:17]([NH:16][C@H:10]1[C:9]2[C:13](=[CH:14][CH:15]=[C:7]([C:5]([OH:6])=[O:4])[CH:8]=2)[CH2:12][CH2:11]1)=[O:25]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 25 °C
Procedure
Method 1 LiOH (5 eq) was added to a suspension of (3R)-3-[(2-chloro-benzoyl)amino]-2,3-dihydro-1H-indene-5-carboxylic acid methyl ester (B-01) (8.569 mmol, 1 eq) in methanol (35 ml) and water (8 ml), and the reaction mixture was stirred overnight at 25° C. Methanol was removed in vacuo and the residue was taken up in diethyl ether and water. The phases were separated and the aqueous phase was adjusted to pH 2 with 1N HCl. The aqueous phase was extracted with ethyl acetate (2×) and the combined organic phases were then dried over magnesium sulfate. After concentration, the desired product (3R)-3-[(2-chloro-benzoyl)amino]-2,3-dihydro-1H-indene-5-carboxylic acid (E-01) was obtained. Yield: 93%
Workup
- customMethanol was removed in vacuo
- customThe phases were separated
- extractionThe aqueous phase was extracted with ethyl acetate (2×)
- dry with materialthe combined organic phases were then dried over magnesium sulfate
- concentrationAfter concentration
Sources & evidence
- ORD record
- ord-de309ea26d2a44188b13b92fcc326b35
- Source dataset
- uspto-grants-2014_03
- Patent number
- US08680159B2
Reaction notes
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