Water → HCID 57528977, compound

HRID 1454047Notes

Reaction equation

HRID 1454047 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]=[CH2:14])[CH:8]=2)=[N:4][C:3]=1[CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[C@H:23]([CH2:27][C:28]([O:30]CC)=[O:29])[CH2:22][CH2:21]2.[Li+].[OH-].O>C(O)C.C1COCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([CH:13]=[CH2:14])[CH:8]=2)=[N:4][C:3]=1[CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]2[C:24](=[CH:25][CH:26]=1)[C@H:23]([CH2:27][C:28]([OH:30])=[O:29])[CH2:22][CH2:21]2

Participants

6

Reactant 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 57528927HCID 57528927, compound

Product 1

HCID 57528977HCID 57528977, compoundYield 74.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl ((1S)-5-{2-[5-methyl-2-(3-vinylphenyl)-1,3-oxazol-4-yl]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetate (40 mg, 0.09 mmol) in ethanol (1.0 mL) and THF (1.0 mL) was added LiOH (39 mg) followed by water (1 mL). The reaction mixture was then stirred at rt for 4 h. The reaction mixture was then acidified to pH 5-6 and concentrated under reduced pressure. The residue redissolved in methanol, and filtered through a C8-Silica plug. The filtrate was then purified by preparative HPLC using with 10 to 70% acetonitrile in water to afford 27.2 mg (72%) of desired product. 1H NMR (CD2Cl2) δ 7.97 (s, 1H), 7.79 (d, 1H), 7.42 (d, 1H), 7.35 (t, 1H), 7.02 (d, 1H), 6.62-6.76 (m, 3H), 5.80 (d, 1H), 5.27 (d, 1H), 4.14 (t, 2H), 3.43 (qr, 1H), 2.90 (t, 2H), 2.66-2.83 (m, 3H), 2.29-2.43 (m, 5H), 1.67-1.72 (m, 1H). EI-LCMS(rel abundance), RT=3.95, m/z 404.4 (MH+, 72%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue redissolved in methanol
  3. filtrationfiltered through a C8-Silica plug
  4. customThe filtrate was then purified by preparative HPLC

Sources & evidence

ORD record
ord-5846d3de8335462d8488f926d220016c
Source dataset
uspto-grants-2009_01
Patent number
US07476742B2

Reaction notes

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