Lithium hydroxide, monohydrate → HCID 86628124, compound

HRID 2190332Notes

Reaction equation

HRID 2190332 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]([C@H:28]1[CH2:32][CH2:31][C@H: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]([C@H:28]1[CH2:32][CH2:31][C@H: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 86628125HCID 86628125, compound

Product 1

HCID 86628124HCID 86628124, compound

Reagents, catalysts & solvents 1

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

Conditions

Temperature
55 °C

Procedure

To a solution of (1S,3S)-methyl 3-(3-(benzo[d]thiazol-2-yl)-1-(3,3-diphenylpropyl)ureido)cyclopentanecarboxylate 42 (303 mg, 589 μmol) in 8:1 MeOH/H2O (18 ml) was added lithium hydroxide hydrate (49.5 mg, 1180 μmol). The reaction mixture was stirred for overnight at 55° C. Volatiles were removed by concentration under reduced pressure. The leftover residue was treated with 10 mL water and 10 mL of aqueous 10% HCl. A precipitate formed upon addition of the acid. After standing for 10 min the precipitate was filtered and washed with copious of amounts of water. After drying under vacuum, the precipitate was purified by injection as a solution in DMF on a reverse phase HPLC column using 5->95% CH3CN/0.1% aqueous TFA as eluant. Product 43 was isolated as white solid (250 mg). 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 treated with 10 mL water and 10 mL of aqueous 10% HCl
  3. customA precipitate formed upon addition of the acid
  4. waitAfter standing for 10 min
  5. filtrationthe precipitate was filtered
  6. washwashed with copious of amounts of water
  7. customAfter drying under vacuum
  8. customthe precipitate was purified by injection as a solution in DMF on a reverse phase HPLC column

Sources & evidence

ORD record
ord-a9a8c8aeff064897a8fccf97354a43cf
Source dataset
uspto-grants-2012_12
Patent number
US08324396B2

Reaction notes

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