Water → HCID 57528966, compound

HRID 1454042Notes

Reaction equation

HRID 1454042 reaction equation
[CH3:1][N:2]([CH3:34])[C:3]1[CH:4]=[C:5]([C:10]2[O:11][C:12]([CH3:33])=[C:13]([CH2:15][CH2:16][O:17][C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[C@H:23]([CH2:27][C:28]([O:30]CC)=[O:29])[CH2:22][CH2:21]4)[N:14]=2)[CH:6]=[CH:7][C:8]=1[CH3:9].[Li+].[OH-].O>C(O)C.C1COCC1>[CH3:34][N:2]([CH3:1])[C:3]1[CH:4]=[C:5]([C:10]2[O:11][C:12]([CH3:33])=[C:13]([CH2:15][CH2:16][O:17][C:18]3[CH:19]=[C:20]4[C:24](=[CH:25][CH:26]=3)[C@H:23]([CH2:27][C:28]([OH:30])=[O:29])[CH2:22][CH2:21]4)[N:14]=2)[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57528915HCID 57528915, compound

Product 1

HCID 57528966HCID 57528966, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl [(1S)-5-(2-{2-[3-(dimethylamino)-4-methylphenyl]-5-methyl-1,3-oxazol-4-yl}ethoxy)-2,3-dihydro-1H-inden-1-yl]acetate (175.0 mg, 0.38 mmol) in ethanol (1 mL) and THF (1 mL) was added LiOH (159 mg) followed by addition of 1 mL water. The reaction mixture was then stirred at rt for 4 h. The reaction mixture was then acidified to pH 5-6 and the solvent was removed by reduced pressure. The residue was redissolved in methanol, filtered through a plug of C8-Silica plug before preparative HPLC purification using 10 to 70% acetonitrile in water to afford desired product 156 mg (95% yield). 1H NMR (300 MHz/CD2Cl2) δ 7.96 (s, 1H), 7.80 (d, 1H), 7.35 (d, 1H), 7.06 (d, 1H), 6.77 (s, 1H), 6.67 (d, 1H), 4.21 (t, 2H), 3.47 (qr, 1H), 3.11 (s, 6 H), 2.97 (t, 2H), 2.75-2.90 (m, 2H), 2.70 (dd, 1H), 2.54 (s, 3H), 2.29-2.46 (m, 5H), 1.65-1.78 (m, 1H). EI-LCMS(rel abundance), m/z 435.4 (MH+, 100%). HPLC RT: 3.52 min.

Workup

  1. customthe solvent was removed by reduced pressure
  2. dissolutionThe residue was redissolved in methanol
  3. filtrationfiltered through a plug of C8-Silica plug before preparative HPLC purification

Sources & evidence

ORD record
ord-73c487dee33d463aba79e1b32e68544e
Source dataset
uspto-grants-2009_01
Patent number
US07476742B2

Reaction notes

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