Ammonium Hydroxide → HCID 71246633, compound

HRID 1519098Notes

Reaction equation

HRID 1519098 reaction equation
C[N:2]([CH:21]1[CH:28]2[CH2:29][C:24]3([C:31](O)=[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].C[CH2:35][N:36]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[NH4+].[OH-]>C(Cl)Cl.O>[CH3:35][NH:36][C:31]([C:24]12[CH2:29][CH:28]3[CH2:27][CH:26]([CH2:30][CH:22]([CH:21]3[NH:2][C:3](=[O:20])[C:4]([N:7]([CH2:18][CH3:19])[S:8]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[CH3:17])(=[O:9])=[O:10])([CH3:6])[CH3:5])[CH2:23]1)[CH2:25]2)=[O:32]

Participants

7

Reactant 4

HCID 14923Ammonium HydroxideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 71246169HCID 71246169, compound

Product 1

HCID 71246633HCID 71246633, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

N-methyl-4-(2-(N-ethyl-2-methylphenylsulfonamido)-2-methylpropanamido)adamantane-1-carboxylic acid (380 mg, 0.82 mmol) was dissolved in CH2Cl2 (10 ml), and added with EDCI (314 mg, 1.64 mmol) and HOBT (222 mg, 1.64 mmol), followed by stirring for 30 minutes. 30% NH4OH aqueous solution (5 ml) was added thereto, followed by stirring at room temperature for 12 hours. The resultant solution was added with H2O, extracted with CH2Cl2 (×3), dried with MgSO4, and filtered. Through vacuum distillation, the solvent was removed. The resultant mixture was purified with column chromatography so as to obtain N-methyl-4-(2-(N-ethyl-2-methylphenylsulfonamido)-2-methylpropanamido)adamantane-1-carboxamide (296 mg, 0.64 mmol, 78%).

Workup

  1. stirringby stirring at room temperature for 12 hours
  2. extractionextracted with CH2Cl2 (×3)
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. distillationThrough vacuum distillation
  6. customthe solvent was removed
  7. customThe resultant mixture was purified with column chromatography so as

Sources & evidence

ORD record
ord-75df31a2afaf40e892405c50c4a516b3
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

Loading…