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

HRID 396036Notes

Reaction equation

HRID 396036 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:44][Si](CC)(CC)CC)[CH2:16][NH:17][CH2:18][CH2:19][C:20]2[CH:43]=[CH:42][C:23]([NH:24][CH:25]3[CH2:30][CH2:29][N:28]([C:31]([NH:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41])=[O:32])[CH2:27][CH2:26]3)=[CH:22][CH:21]=2)=[CH:11][C:10]=1[NH:52][S:53]([CH3:56])(=[O:55])=[O:54])C1C=CC=CC=1.[F-].C([NH3+])(C)(C)C>O1CCCC1>[CH2:34]([NH:33][C:31]([N:28]1[CH2:29][CH2:30][CH:25]([NH:24][C:23]2[CH:42]=[CH:43][C:20]([CH2:19][CH2:18][NH:17][CH2:16][C@H:15]([OH:44])[C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([NH:52][S:53]([CH3:56])(=[O:55])=[O:54])[CH:11]=3)=[CH:21][CH:22]=2)[CH2:26][CH2:27]1)=[O:32])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

4

Reactant 2

HCID 21866379t-Butylammonium fluorideHCID 699858334-{4-[2-({(2r)-2-{4-(Benzyloxy)-3-[(methylsulfonyl)amino]phenyl}-2-[(triethylsilyl)oxy]ethyl}amino)ethyl]anilino}-n-octyl-1-piperidinecarboxamide

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

4-{4-[2-({(2R)-2-{4-(Benzyloxy)-3-[(methylsulfonyl)amino]phenyl}-2-[(triethylsilyl)oxy]ethyl}amino)ethyl]anilino}-N-octyl-1-piperidinecarboxamide was dissolved in anhydrous tetrahydrofuran and tert-butylammonium fluoride (1M in tetrahydrofuran) added. The reaction was stirred at ambient temperature for 4 days. The solvent was removed in vacuo and the residue purified by flash chromatography on silica gel Merck-60 (eluant: 20:1 going to 10:1 chloroform-methanol containing 2% triethylamine) to furnish the title compound (0.36 g, 0.519 mmol).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by flash chromatography on silica gel Merck-60 (eluant: 20:1 going to 10:1 chloroform-methanol containing 2% triethylamine)

Sources & evidence

ORD record
ord-99fb72df24b343b69e596d04d0afc4a2
Source dataset
uspto-grants-2003_08
Patent number
US06605618B2

Reaction notes

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