Lithium hydroxide, monohydrate → HCID 25175140, compound

HRID 2190331Notes

Reaction equation

HRID 2190331 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11](=[O:37])[N:12]([CH:28]1[CH2:32][CH2:31][CH:30]([C:33]([O:35]C)=[O:34])[CH2:29]1)[CH2:13][CH2:14][CH:15]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.O.[OH-].[Li+]>CO.O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11](=[O:37])[N:12]([CH:28]1[CH2:32][CH2:31][CH:30]([C:33]([OH:35])=[O:34])[CH2:29]1)[CH2:13][CH2:14][CH:15]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86628123HCID 86628123, compound

Product 1

HCID 25175140HCID 25175140, compound

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
55 °C

Procedure

To a solution of methyl 3-(3-(benzo[d]thiazol-2-yl)-1-(3,3-diphenylpropyl)ureido)cyclopentanecarboxylate 35 (308 mg, 600 μmol) in 10:1 MeOH/H2O (5.5 ml) was added lithium hydroxide hydrate (50.3 mg, 1199 μmol). The reaction mixture was stirred for overnight at 55° C. Volatiles were removed by concentration under reduced pressure. The leftover residue was solubilized with 60 mL of a 1:1 mixture of Water and Ethyl Acetate. An additional 2 mL of 2M KOH was added. The organic phase was separated and the aqueous phase was extracted further with ethyl acetate (2×20 mL). The organic extracts were discarded and the aqueous layer was acidified with 10 mL of 10% aqueous HCl and extracted with ethyl acetate (3×20 mL). The combined organic extracts were dried with magnesium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica using 10->45% EtOAc/Hexanes as eluant to afford 36 as a white solid. LCMS (ES) calcd for C29H29N3O3S 499.2 found 500.2 (MH+).

Workup

  1. customVolatiles were removed by concentration under reduced pressure
  2. additionThe leftover residue was solubilized with 60 mL of a 1:1 mixture of Water and Ethyl Acetate
  3. additionAn additional 2 mL of 2M KOH was added
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted further with ethyl acetate (2×20 mL)
  6. extractionextracted with ethyl acetate (3×20 mL)
  7. dry with materialThe combined organic extracts were dried with magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by chromatography on silica using 10->45% EtOAc/Hexanes as eluant

Sources & evidence

ORD record
ord-b4f9e266ead2492d96cdc922f5c049ec
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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