Lithium hydroxide, monohydrate → HCID 54759712, compound

HRID 1894761Notes

Reaction equation

HRID 1894761 reaction equation
[CH3:1][N:2]([CH3:32])[CH:3]([CH2:30][CH3:31])[CH:4]([C:10]1[CH:29]=[CH:28][C:13]2[N:14]=[C:15]([NH:17][CH2:18][C:19]([CH3:27])([CH3:26])[C:20]([O:22]C(C)C)=[O:21])[S:16][C:12]=2[CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1.O.[OH-].[Li+]>O1CCOCC1.O>[CH3:32][N:2]([CH3:1])[CH:3]([CH2:30][CH3:31])[CH:4]([C:10]1[CH:29]=[CH:28][C:13]2[N:14]=[C:15]([NH:17][CH2:18][C:19]([CH3:26])([CH3:27])[C:20]([OH:22])=[O:21])[S:16][C:12]=2[CH:11]=1)[N:5]1[CH:9]=[CH:8][N:7]=[CH:6]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 54760072HCID 54760072, compound

Product 1

HCID 54759712HCID 54759712, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture isopropyl 3-((6-(2-(dimethylamino)-1-(1H-imidazol-1-yl)butyl)-benzo[d]thiazol-2-yl)amino)-2,2-dimethylpropanoate (30 mg, 0.065 mmol) in 300 μL dioxane and 300 μL water was treated with lithium hydroxide monohydrate (21.4 mg, 0.57 mmol) and heated at 100° C. for 1 hr. The mixture was concentrated in vacuo and the residue dissolved in about 2 mL of water. The solution was neutralized with 1N HCl then concentrated again in vacuo. The residue was purified by PTLC using two, 1 mm silica plates eluting with 10% MeOH/DCM to give the title compounds. MS (ESI−) m/z 414.98 [M−H]−

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in about 2 mL of water
  3. concentrationthen concentrated again in vacuo
  4. customThe residue was purified by PTLC
  5. washeluting with 10% MeOH/DCM

Sources & evidence

ORD record
ord-f0a57b4eab3b429fabcc92c499d0a03d
Source dataset
uspto-grants-2013_08
Patent number
US08513291B2

Reaction notes

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