Hydrochloric Acid → HCID 10127704, compound

HRID 1454044Notes

Reaction equation

HRID 1454044 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:19][CH2:20][O:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[C@H:27]([CH2:31][C:32]([O:34]CC)=[O:33])[CH2:26][CH2:25]2.O[Li].O.O.Cl>CCO.C1COCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([N:13]3[CH2:14][CH2:15][O:16][CH2:17][CH2:18]3)=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:19][CH2:20][O:21][C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[C@H:27]([CH2:31][C:32]([OH:34])=[O:33])[CH2:26][CH2:25]2

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 57528992HCID 57528992, compound

Product 1

HCID 10127704HCID 10127704, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl [(1S)-5-(2-{5-methyl-2-[4-(4-morpholinyl)phenyl]-1,3-oxazol-4-yl}ethoxy)-2,3-dihydro-1H-inden-1-yl]acetate (0.058 g, 0.12 mmol) was dissolved in EtOH (1 mL), and LiOH.H2O (0.025 g, 0.6 mmol) was added. Water (1 mL) was added, followed by THF was added until the cloudy solution became clear. The resulting mixture was stirred overnight at rt. HCl (2 N) was added to adjust the pH to 2, and the mixture was extracted three times with ethyl acetate. The combined organic layers were dried, filtered and evaporated. The residue was purified by preparative HPLC to obtain [(1S)-5-(2-{5-methyl-2-[4-(4-morpholinyl)phenyl]-1,3-oxazol-4-yl}ethoxy)-2,3-dihydro-1 H-inden-1-yl]acetic acid (0.038 g, 0.08 mmol) in 70% yield. 1H NMR ((CDCl3) δ 1.8 (m, 1H), 2.4 (m, 3H), 3.0 (t, 2H), 3.3 (m, 4H), 3.5 (m, 1H), 3.9 (m, 4H), 4.2 (t, 2H), 6.7 (m, 1H), 6.8 (s, 1H), 6.9 (d, 2H), 7.1 (d, 1H), 7.9 (d, 2H); MS (ES) 463 (M+1)+.

Workup

  1. additionwas added until the cloudy solution
  2. extractionthe mixture was extracted three times with ethyl acetate
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-6299f7ae01f84f9086e221e6cbac38da
Source dataset
uspto-grants-2009_01
Patent number
US07476742B2

Reaction notes

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