Lithium Hydroxide → HCID 10366556, compound

HRID 603437Notes

Reaction equation

HRID 603437 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([C:8]2[CH:33]=[CH:32][C:11]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[C@H:22]([CH2:26][C:27]([O:29]CC)=[O:28])[CH2:21][CH2:20]4)=[C:10]([O:34][CH3:35])[CH:9]=2)[O:6][CH:7]=1)[CH3:2].[Li+].[OH-]>C1COCC1.O.CCO>[CH2:1]([C:3]1[N:4]=[C:5]([C:8]2[CH:33]=[CH:32][C:11]([O:12][CH2:13][CH2:14][CH2:15][O:16][C:17]3[CH:18]=[C:19]4[C:23](=[CH:24][CH:25]=3)[C@H:22]([CH2:26][C:27]([OH:29])=[O:28])[CH2:21][CH2:20]4)=[C:10]([O:34][CH3:35])[CH:9]=2)[O:6][CH:7]=1)[CH3:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 59300484HCID 59300484, compound

Product 1

HCID 10366556HCID 10366556, compoundYield 77.2%

Reagents, catalysts & solvents 1

HCID 18504229Ethanol tetrahydrofuran waterSolvent

Procedure

To a solution of ethyl ((1S)-5-{3-[4-(4-ethyl-1,3-oxazol-2-yl)-2-methoxyphenoxy]propoxy}-2,3-dihydro-1H-inden-1-yl)acetate (52.2 mg, 0.109 mmol) (Example 173) in THF/water/EtOH (1:2:1, 4 mL) was added LiOH (5.2 mg, 0.218 mmol). The solution was stirred at rt for 3 h and concentrated under reduced pressure. The residue was diluted with water and acidified using HCl (2 N aqueous solution), resulting in precipitation of a white solid. The solid was collected by filtration and dried to give 38.0 mg (77%) of the title compound. 1H NMR (400 MHz, CD2Cl2): δ 7.82 (s, 1H), 7.66 (d, 1H), 7.47 (s, 1H), 7.07 (d, 1H), 6.98 (d, 1H), 6.79 (s, 1H), 6.70 (d. 1H), 4.28 (t, 2H), 4.19 (t, 2H), 3.94 (s, 3H), 3.51 (m, 1H), 2.91 (m, 2H), 2.75 (m, 3H), 2.50 (m, 1H), 2.40 (m, 1H), 2.30 (m, 2H), 1.79 (m, 1H), 1.34 (t, 3H); LC-MS: RT=3.31 min, (M+H)+ 452.1.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with water
  3. customresulting in precipitation of a white solid
  4. filtrationThe solid was collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-47661bc354064cc7af42ca893400ad44
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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