Diisopropylethylamine → 4-(4-{2-[(2r)-2-Hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic acidoctylamide

HRID 396035Notes

Reaction equation

HRID 396035 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:18][Si](CC)(CC)CC)[CH2:16]I)=[CH:11][C:10]=1[NH:26][S:27]([CH3:30])(=[O:29])=[O:28])C1C=CC=CC=1.[NH2:31][CH2:32][CH2:33][C:34]1[CH:57]=[CH:56][C:37]([NH:38][CH:39]2[CH2:44][CH2:43][N:42]([C:45]([NH:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55])=[O:46])[CH2:41][CH2:40]2)=[CH:36][CH:35]=1.C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:48]([NH:47][C:45]([N:42]1[CH2:41][CH2:40][CH:39]([NH:38][C:37]2[CH:36]=[CH:35][C:34]([CH2:33][CH2:32][NH:31][CH2:16][C@H:15]([OH:18])[C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:26][S:27]([CH3:30])(=[O:28])=[O:29])[CH:11]=3)=[CH:57][CH:56]=2)[CH2:44][CH2:43]1)=[O:46])[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH3:55]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 181736624-[4-(2-Aminoethyl)anilino]-N-octyl-1-piperidinecarboxamideHCID 54211801(R)-N-[2-benzyloxy-5-(2-iodo-1-triethylsilyloxyethyl)phenyl]methanesulfonamide

Product 1

HCID 101889984-(4-{2-[(2r)-2-Hydroxy-2-(4-hydroxy-3-methanesulfonylamino-phenyl)-ethylamino]-ethyl}-phenylamino)-piperidine-1-carboxylic acidoctylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(2-(Benzyloxy)-5-{(1R)-2-iodo-1-[(triethylsilyl)oxy]ethyl}phenyl)methanesulfonamide (E. J. Corey and J. O. Link, J. Org. Chem., 1991, 56, 422 and WO 9737646) (1.0 g, 1.93 mmol) was refluxed in anhydrous tetrahydrofuran (30 mL) with 4-[4-(2-aminoethyl)anilino]-N-octyl-1-piperidinecarboxamide (1.48 g, 3.98 mmol) and N,N-diisopropylethylamine (0.69 mL). The reaction was stirred at reflux for 7 days. The solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel Merck-60 (eluant: 20:1 chloroform-methanol containing 2% triethylamine) to furnish the title compound (0.92 g, 1.14 mmol).

Workup

  1. temperatureat reflux for 7 days
  2. customThe solvent was removed in vacuo
  3. customthe residue was purified by flash chromatography on silica gel Merck-60 (eluant: 20:1 chloroform-methanol containing 2% triethylamine)

Sources & evidence

ORD record
ord-3c3e909bd0dc42c1a6390d4d6d45b78e
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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