2-Aminoadamantane hydrochloride → N-(adamantane-2-yl)-1-(2-nitrophenylsulfonamido)cyclobutanecarboxyamide

HRID 1519079Notes

Reaction equation

HRID 1519079 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:13][C:14]1([C:18](O)=O)[CH2:17][CH2:16][CH2:15]1)(=[O:12])=[O:11])([O-:3])=[O:2].Cl.[CH:22]12[CH2:31]C3[CH2:27][CH:28]([CH2:30]C(C3)[CH:23]1N)[CH2:29]2.F[P-](F)(F)(F)(F)F.N1([O:49][P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.CC[N:62]([CH:66]([CH3:68])[CH3:67])[CH:63](C)C>C(Cl)Cl>[CH:68]12[CH2:31][CH:22]3[CH2:29][CH:28]([CH2:30][CH:67]([CH2:23]3)[CH:66]1[NH:62][C:63]([CH2:18][C:14]1([NH:13][S:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N+:1]([O-:3])=[O:2])(=[O:11])=[O:12])[CH2:15][CH2:16][CH2:17]1)=[O:49])[CH2:27]2

Participants

6

Reactant 4

HCID 253312-Aminoadamantane hydrochlorideHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 712467071-(2-Nitrophenylsulfonamido)cyclobutanecarboxylic acid

Product 1

HCID 131733091N-(adamantane-2-yl)-1-(2-nitrophenylsulfonamido)cyclobutanecarboxyamideYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 10-mL flask, 1-(2-nitrophenylsulfonamido)cyclobutanecarboxylic acid (200 mg, 0.666 mmol), 2-adamantanamine hydrochloride (150 mg, 0.799 mmol), and BOP (295 mg, 0.667 mmol) were charged, and CH2Cl2 (3 ml) was charged, followed by stirring for 30 minutes at room temperature. DIPEA (0.28 ml, 1.60 mmol) was added thereto, followed by stirring at room temperature for 12 hours. After the reaction was completed, the organic layer was separated using CH2Cl2 and H2O, dried with MgSO4, and filtered. The resultant mixture was purified with column chromatography (EA/n-Hex=1:2) to obtain N-(adamantane-2-yl)-1-(2-nitrophenylsulfonamido)cyclobutanecarboxyamide (282 mg, 97%).

Workup

  1. stirringby stirring at room temperature for 12 hours
  2. customthe organic layer was separated
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customThe resultant mixture was purified with column chromatography (EA/n-Hex=1:2)

Sources & evidence

ORD record
ord-67341d6b541d45e68a8f5098cf883529
Source dataset
uspto-grants-2015_07
Patent number
US09073830B2

Reaction notes

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