Lithium Hydroxide → 4-[3-(4-Trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane-9-sulfonyl]-indan-2-carboxylic acid

HRID 2110159Notes

Reaction equation

HRID 2110159 reaction equation
C1C2C(=CC=CC=2)CC1C(O)=O.C[O:14][C:15]([CH:17]1[CH2:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][C:23]=2[S:26]([N:29]2[CH:34]3[CH2:35][CH2:36][CH2:37][CH:30]2[CH2:31][N:32]([C:38]2[CH:43]=[CH:42][C:41]([O:44][C:45]([F:48])([F:47])[F:46])=[CH:40][CH:39]=2)[CH2:33]3)(=[O:28])=[O:27])[CH2:18]1)=[O:16].[Li+].[OH-].FC(F)(F)C1C=CC(C2CCNCC=2)=CC=1>CO.O1CCCC1>[F:48][C:45]([F:46])([F:47])[O:44][C:41]1[CH:40]=[CH:39][C:38]([N:32]2[CH2:33][CH:34]3[N:29]([S:26]([C:23]4[CH:22]=[CH:21][CH:20]=[C:19]5[C:24]=4[CH2:25][CH:17]([C:15]([OH:16])=[O:14])[CH2:18]5)(=[O:28])=[O:27])[CH:30]([CH2:37][CH2:36][CH2:35]3)[CH2:31]2)=[CH:43][CH:42]=1

Participants

7

Reactant 4

HCID 3939Lithium HydroxideHCID 5757772-Indancarboxylic AcidHCID 12440708Pyridine, 1,2,3,6-tetrahydro-4-[4-(trifluoromethyl)phenyl]-HCID 670457844-[3-(4-Trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane-9-sulfonyl]-indan-2-carboxylic acid methyl ester

Product 1

HCID 576359654-[3-(4-Trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane-9-sulfonyl]-indan-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-|3-(4-trifluoromethoxy-phenyl)-3,9-diaza-bicyclo|3.3.1|nonane-9-sulfonyl|-indan-2-carboxylic acid: A mixture of 4-[3-(4-trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane-9-sulfonyl]-indan-2-carboxylic acid methyl ester (13 mg, 0.025 mmol), 1N LiOH (2 mL), tetrahydrofuran (8 mL), and methanol (2 mL) was stirred at rt for 3 h. The reaction was poured into 1N HCl (40 mL) and extracted with ethyl acetate (40 mL×2). The combined organic extracts were dried, filtered, and concentrated to give 4-[3-(4-trifluoromethoxy-phenyl)-3,9-diaza-bicyclo[3.3.1]nonane-9-sulfonyl]-indan-2-carboxylic acid: 1H NMR (400 MHz, DMSO-d6): δ7.69 (d, 1H), 7.52 (d, 1H), 7.38 (t, 1H), 7.19 (d, 2H), 6.92 (d, 2H), 4.04-3.97 (m, 2H), 3.74-3.67 (m, 2H), 3.44-3.30 (m, 3H), 3.26-3.10 (m, 2H), 2.96-2.86 (m, 2H), 2.26-2.15 (m, 1H), 1.86-1.72 (m, 4H), 1.51-1.43 (m, 1H); MS (ESI): 511.4 (M+H).

Workup

  1. extractionextracted with ethyl acetate (40 mL×2)
  2. customThe combined organic extracts were dried
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-4e9ed4a5b27a48e2ace5d92784796e25
Source dataset
uspto-grants-2009_04
Patent number
US07517884B2

Reaction notes

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