Methanol → HCID 71246169, compound

HRID 1519097Notes

Reaction equation

HRID 1519097 reaction equation
[CH3:1][N:2]([CH:21]1[CH:28]2[CH2:29][C:24]3([C:31]([O-:33])=[O:32])[CH2:25][CH:26]([CH2:30][CH:22]1[CH2:23]3)[CH2:27]2)[C:3](=[O:20])[C:4]([N:7]([CH2:18][CH3:19])[S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])(=[O:10])=[O:9])([CH3:6])[CH3:5].C1COCC1.CO.O[Li].O>O>[CH3:1][N:2]([CH:21]1[CH:22]2[CH2:23][C:24]3([C:31]([OH:33])=[O:32])[CH2:25][CH:26]([CH2:27][CH:28]1[CH2:29]3)[CH2:30]2)[C:3](=[O:20])[C:4]([N:7]([CH2:18][CH3:19])[S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:17])(=[O:9])=[O:10])([CH3:5])[CH3:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 86727918HCID 86727918, compound

Product 1

HCID 71246169HCID 71246169, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

N-methyl-4-(2-(N-ethyl-2-methylphenylsulfonamido)-2-methylpropanamido)adamantane-1-carboxylate (400 mg, 0.84 mmol) was charged, and dissolved through addition of THF (5 ml), and methanol (5 ml). LiOH.H2O dissolved in H2O (4 ml) was added thereto, followed by stirring for 12 hours at room temperature. After stirring for 12 hours, the resultant solution was vacuum-evaporated, acidified with 2N—HCl to pH 2˜3, and extracted with EA (×2). The organic layer was dried with MgSO4, and filtered. Through vacuum distillation, the solvent was removed so as to obtain N-methyl-4-(2-(N-ethyl-2-methylphenylsulfonamido)-2-methylpropanamido)adamantane-1-carboxylic acid (380 mg, 0.82 mmol, 98%).

Workup

  1. additionwas added
  2. stirringAfter stirring for 12 hours
  3. customthe resultant solution was vacuum-evaporated
  4. extractionextracted with EA (×2)
  5. dry with materialThe organic layer was dried with MgSO4
  6. filtrationfiltered
  7. distillationThrough vacuum distillation
  8. customthe solvent was removed so as

Sources & evidence

ORD record
ord-17d584ff2b34458ea99daa35b9a16e6c
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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