Methanol → HCID 71246636, compound

HRID 1519071Notes

Reaction equation

HRID 1519071 reaction equation
[CH3:1][C:2]([NH:20][S:21]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)(=[O:23])=[O:22])([CH3:19])[C:3]([NH:5][CH:6]1[CH:13]2[CH2:14][C:9]3([C:16]([O-:18])=[O:17])[CH2:10][CH:11]([CH2:15][CH:7]1[CH2:8]3)[CH2:12]2)=[O:4].C1COCC1.CO.O[Li].O>O>[CH3:19][C:2]([NH:20][S:21]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)(=[O:23])=[O:22])([CH3:1])[C:3]([NH:5][CH:6]1[CH:13]2[CH2:14][C:9]3([C:16]([OH:18])=[O:17])[CH2:10][CH:11]([CH2:15][CH:7]1[CH2:8]3)[CH2:12]2)=[O:4]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86727915HCID 86727915, compound

Product 1

HCID 71246636HCID 71246636, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 50-mL flask, 4-(2-methyl-2-(phenylsulfonamido)propanamido)adamantane-1-carboxylate (500 mg, 1.94 mmol) was charged, and dissolved through addition of THF (6 ml), and methanol (6 ml). LiOH.H2O dissolved in H2O (6 ml) was added thereto, followed by stirring for 12 hours at room temperature. After the stirring for 12 hours, the resultant solution was vacuum-evaporated, acidified with 2N—HCl to pH 1˜2, and extracted with addition of EA (20 ml). The organic layer was dried with MgSO4, and filtered. Then, through vacuum distillation, the solvent was removed so as to obtain 4-(2-methyl-2-(phenylsulfonamido)propanamido)adamantane-1-carboxylic acid compound (402 mg, 85%).

Workup

  1. additionwas added
  2. waitAfter the stirring for 12 hours
  3. customthe resultant solution was vacuum-evaporated
  4. extractionextracted with addition of EA (20 ml)
  5. dry with materialThe organic layer was dried with MgSO4
  6. filtrationfiltered
  7. distillationThen, through vacuum distillation
  8. customthe solvent was removed so as

Sources & evidence

ORD record
ord-08ec73a71d8b41ed836d84b57a242ad3
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

Loading…