Methanol → HCID 71246296, compound

HRID 1519088Notes

Reaction equation

HRID 1519088 reaction equation
C[O:2][C:3]([C:5]12[CH2:14][CH:9]3[CH2:10][CH:11]([CH2:13][CH:7]([CH:8]3[NH:15][C:16]([C:18]3([NH:24][S:25]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[Br:34])(=[O:27])=[O:26])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[O:17])[CH2:6]1)[CH2:12]2)=[O:4].O1CCCC1.CO.[OH-].[Li+]>O>[Br:34][C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[S:25]([NH:24][C:18]1([C:16]([NH:15][CH:8]2[CH:7]3[CH2:6][C:5]4([C:3]([OH:4])=[O:2])[CH2:12][CH:11]([CH2:10][CH:9]2[CH2:14]4)[CH2:13]3)=[O:17])[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1)(=[O:27])=[O:26]

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 71248884HCID 71248884, compound

Product 1

HCID 71246296HCID 71246296, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a 25-mL flask, 4-{[1-(2-bromo-benzenesulfonylamino)-cyclohexanecarbonyl]-amino}-adamantane-1-carboxylic acid methylester (140 mg, 0.253 mmol) was charged, and dissolved through addition of tetrahydrofuran (5 mL), and methanol (5 mL). Lithium hydroxide dissolved in purified water (5 mL) was added thereto, followed by stirring for 12 hours at room temperature. After the reaction was completed, the resultant solution was vacuum-evaporated, acidified with 2N hydrochloric acid aqueous solution to pH 1-2, and extracted with addition of ethyl acetate (20 ml). The organic layer was added with magnesium sulfate so as to remove remaining moisture. Through filtering and vacuum distillation, the solvent was removed so as to obtain 4-{[1-(2-bromo-benzenesulfonylamino)-cyclohexanecarbonyl]-amino}-adamantane-1-carboxylic acid (106 mg, 79%).

Workup

  1. additionwas added
  2. customthe resultant solution was vacuum-evaporated
  3. extractionextracted with addition of ethyl acetate (20 ml)
  4. additionThe organic layer was added with magnesium sulfate so as
  5. customto remove
  6. filtrationThrough filtering
  7. distillationvacuum distillation
  8. customthe solvent was removed so as

Sources & evidence

ORD record
ord-ad26446a062c4d01905c430e9c04b80f
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

Loading…