Water → HCID 59300520, compound

HRID 603464Notes

Reaction equation

HRID 603464 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([N:16]([CH3:36])[CH2:17][CH2:18][CH2:19][O:20][C:21]4[CH:22]=[C:23]5[C:27](=[CH:28][CH:29]=4)[C@H:26]([CH2:30][C:31]([O:33]CC)=[O:32])[CH2:25][CH2:24]5)[N:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.O.O[Li].O>C1COCC1.C(O)C>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[CH:15]=[CH:14][N:13]=[C:12]([N:16]([CH3:36])[CH2:17][CH2:18][CH2:19][O:20][C:21]4[CH:22]=[C:23]5[C:27](=[CH:28][CH:29]=4)[C@H:26]([CH2:30][C:31]([OH:33])=[O:32])[CH2:25][CH2:24]5)[N:11]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

6

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 59300419HCID 59300419, compound

Product 1

HCID 59300520HCID 59300520, compoundYield 27.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl ((1S)-5-{3-[[4-(1,3-benzodioxol-5-yl)-2-pyrimidinyl](methyl)amino]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (Example 292, 35 mg, 0.071 mmol) in THF (2 mL), ethanol (1 mL), and water (2 mL) was added LiOH.H2O (7 mg, 0.29 mmol), and the mixture was stirred at rt for 16 h. The reaction mixture was then extracted with Et2O (2×), organic layers discarded, and the remaining aqueous solution was acidified to pH ˜5 using HCl (1 M aqueous solution). The aqueous solution was then extracted with EtOAc. The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure to give 9 mg (27%) of the product. 1H NMR (400 MHz, CDCl3): δ 1.70-1.80 (m, 1H), 2.15-2.20 (m, 2H), 2.32-2.50 (m, 2H), 2.71 (dd, 1H), 2.83-2.95 (m, 2H), 3.30 (s, 3H), 3.51-3.64 (m, 1H), 3.72 (q, 2H), 3.99 (t, 2H), 6.00 (s, 2H), 6.62 (d, 1H), 6.54 (s, 1H), 6.80 (d, 2H), 7.05 (d, 1H), 7.61 (s, 2H), 8.30 (d, 1H); LC-MS: RT=2.50 min, (M+H)+ 462.3.

Workup

  1. extractionThe reaction mixture was then extracted with Et2O (2×), organic layers
  2. extractionThe aqueous solution was then extracted with EtOAc
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f0d6f2748574327a4997611a010f9df
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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