Lithium Hydroxide → HCID 9828518, compound

HRID 1008305Notes

Reaction equation

HRID 1008305 reaction equation
C[O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([OH:28])[C:25]([C:29]3[N:30]=[CH:31][S:32][CH:33]=3)=[CH:24][C:23]=2[CH2:34][CH3:35])[C:12]=1[CH2:36][CH2:37][CH3:38].[OH-].[Li+]>CO>[CH2:34]([C:23]1[CH:24]=[C:25]([C:29]2[N:30]=[CH:31][S:32][CH:33]=2)[C:26]([OH:28])=[CH:27][C:22]=1[O:21][CH2:20][CH2:19][CH2:18][O:17][C:13]1[C:12]([CH2:36][CH2:37][CH3:38])=[C:11]([CH:16]=[CH:15][CH:14]=1)[O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]([OH:39])=[O:2])[CH3:35]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 601112072-{3-[3-(2-Ethyl-5-hydroxy-4-thiazol-4-yl-phenoxy)propoxy]-2-propylphenoxy}benzoic acid methyl ester

Product 1

HCID 9828518HCID 9828518, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-{3-[3-(2-ethyl-5-hydroxy-4-thiazol-4-yl-phenoxy)propoxy]-2-propylphenoxy}benzoic acid methyl ester (130 mg, 0.236 mmol) in methanol (4 mL) was treated with 1 M lithium hydroxide solution at 60° C. for 3 h. The mixture was cooled to room temperature, concentrated in vacuo, and diluted with water. The solution was adjusted to pH ˜4 and extracted three times with methylene chloride. The combined organic layers were dried (sodium sulfate), filtered, and concentrated in vacuo. The residue was dissolved in a minimum of methylene chloride and hexane was added until the solution became cloudy. The mixture was concentrated slowly in vacuo to give 96 mg (76%) of the title compound. 1H NMR (CDCl3) δ 8.90 (s, 1H), 8.23 (dd, J=8, 1 Hz, 1H), 7.41 (m, 2H), 7.38 (s, 1H), 7.29 (m, 2H), 6.82 (d, J=8 Hz, 1H), 6.71 (d, J=3 Hz, 1H), 6.62 (d, J=8 Hz, 1H), 6.54 (s, 1H), 4.25 (t, J=6 Hz, 2H), 4.22 (t, J=6 Hz, 2H), 2.59 (m, 4H), 2.35 (quintet, J=6 Hz, 2H), 1.50 (hextet, J=8 Hz, 2H), 1.19 (t, J=7 Hz, 3H), 0.88 (t, J=8 Hz, 3H); TOF MS ES+ exact mass calculated for C30H32NO6S (p+1): m/z=534.1950. Found: 534.1957. IR (CHCl3, cm−1) 2965, 1738, 1454. Anal. Calcd for C30H31NO6S: C, 67.52; H, 5.86; N. 2.62. Found: C, 67.19; H, 5.72; N, 2.53.

Workup

  1. concentrationconcentrated in vacuo
  2. additiondiluted with water
  3. extractionextracted three times with methylene chloride
  4. dry with materialThe combined organic layers were dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in a minimum of methylene chloride and hexane
  8. additionwas added until the solution
  9. concentrationThe mixture was concentrated slowly in vacuo

Sources & evidence

ORD record
ord-f37f6a7f2f124f3b8be3d02853e8f340
Source dataset
uspto-grants-2004_09
Patent number
US06797723B1

Reaction notes

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