Lithium Hydroxide → HCID 85472222, compound

HRID 2177230Notes

Reaction equation

HRID 2177230 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26]CC)=[O:25])=[C:18]([CH3:29])[C:17]=3[CH3:30])=[C:12]([CH:31]([CH3:33])[CH3:32])[S:11][N:10]=2)=[CH:5][CH:4]=1)[CH3:2].[Li+].[OH-]>O1CCCC1.O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:13]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([OH:26])=[O:25])=[C:18]([CH3:29])[C:17]=3[CH3:30])=[C:12]([CH:31]([CH3:32])[CH3:33])[S:11][N:10]=2)=[CH:7][CH:8]=1)[CH3:2]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 90417631HCID 90417631, compound

Product 1

HCID 85472222HCID 85472222, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Conditions

Temperature
25 °C

Procedure

Into a 25-mL round-bottom flask, was placed ethyl 3-(4-[[3-(4-ethylphenyl)-5-(propan-2-yl)-1,2-thiazol-4-yl]methoxy]-2,3-dimethylphenyl)propanoate (73.1 mg, 0.16 mmol, 1.00 equiv), LiOH (73 mg, 3.05 mmol, 19.42 equiv), tetrahydrofuran/H2O (5 mL). The resulting solution was stirred for 12 h at 25° C. The resulting solution was concentrated. The pH value of the residue was adjusted to 3 with 1M hydrogen chloride. The resulting solution was extracted with 3×40 mL of dichloromethane and the organic layers combined and concentrated. The crude product was purified by Prep-HPLC with the following conditions (1#-Waters 2767-5): Column, SunFire Prep C18, 5 um, 19*100 mm; mobile phase, Water and CH3CN (30% CH3CN up to 90% in 10 min, up to 100% in 2 min, down to 30% in 2 min; Detector, UV 220&254 nm. This resulted in 3.4 mg (5%) of 3-(4-[[3-(4-ethylphenyl)-5-(propan-2-yl)-1,2-thiazol-4-yl]methoxy]-2,3-dimethylphenyl) propanoic acid as a white solid. 1H NMR (300 MHz, CD3OD) δ 7.58 (d, J=8.4 Hz, 2H), 7.26 (d, J=8.1 Hz, 2H), 6.98 (d, J=8.7 Hz, 1H), 6.75 (d, J=8.4 Hz, 1H), 4.94 (s, 2H), 3.44-3.53 (m, 1H), 2.92 (t, J=8.1 Hz, 2H), 2.68 (m, 2H), 2.52 (t, J=7.2 Hz, 2H), 2.24 (s, 3H), 2.10 (s, 3H), 2.14 (s, 6H), 1.25 (t, J=7.5 Hz, 3H). Mass spectrum (ESI, m/z): Calcd. for C26H31NO3S, 438.2 (M+H). found 438.2.

Workup

  1. customInto a 25-mL round-bottom flask, was placed
  2. concentrationThe resulting solution was concentrated
  3. extractionThe resulting solution was extracted with 3×40 mL of dichloromethane
  4. concentrationconcentrated
  5. customThe crude product was purified by Prep-HPLC with the following conditions (1#-Waters 2767-5)
  6. waitmobile phase, Water and CH3CN (30% CH3CN up to 90% in 10 min
  7. waitup to 100% in 2 min
  8. waitdown to 30% in 2 min
  9. customThis resulted in 3.4 mg (5%) of 3-(4-[[3-(4-ethylphenyl)-5-(propan-2-yl)-1,2-thiazol-4-yl]methoxy]-2,3-dimethylphenyl) propanoic acid as a white solid

Sources & evidence

ORD record
ord-0e6c4e3e3cd64d5f832e81c5698128f1
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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