Tetraethylammonium fluoride hydrate → HCID 86751175, compound

HRID 1460090Notes

Reaction equation

HRID 1460090 reaction equation
[CH2:1]([N:4]1[C@@H:9]([CH3:10])[CH2:8][N:7]([C@H:11]([C:26]2[CH:57]=[CH:56][C:29]([C:30]([NH:32][C@H:33]([C:41]([NH:43][C@H:44]([C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[CH2:45][CH:46]([CH3:48])[CH3:47])=[O:42])[CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:31])=[CH:28][CH:27]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][Si](C(C)(C)C)(C)C)[CH:13]=2)[C@H:6]([CH3:58])[CH2:5]1)[CH:2]=[CH2:3].O.[F-].C([N+](CC)(CC)CC)C>C(#N)C>[CH2:1]([N:4]1[C@@H:9]([CH3:10])[CH2:8][N:7]([C@H:11]([C:26]2[CH:57]=[CH:56][C:29]([C:30]([NH:32][C@H:33]([C:41]([NH:43][C@H:44]([C:49]([O:51][C:52]([CH3:53])([CH3:55])[CH3:54])=[O:50])[CH2:45][CH:46]([CH3:48])[CH3:47])=[O:42])[CH2:34][C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:31])=[CH:28][CH:27]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)[C@H:6]([CH3:58])[CH2:5]1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 16211652Tetraethylammonium fluoride hydrateHCID 86751176HCID 86751176, compound

Product 1

HCID 86751175HCID 86751175, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A portion of the benzhydrylpiperazine from above (0.36 g, 0.44 mmol) was stirred with tetraethylammonium fluoride hydrate (0.12 g, 0.67 mmol) in 10 mL of acetonitrile for 1 hr. The solvent was removed and the residue purified by chromatography on silica gel with dichloromethane:ethanol to give 0.180 g (58%) of tert-butyl N-(4-((αR*)-α-((2R*,5S*)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)benzoyl)-L-phenylalanyl-L-leucinate as a white solid.

Workup

  1. customThe solvent was removed
  2. customthe residue purified by chromatography on silica gel with dichloromethane

Sources & evidence

ORD record
ord-328f9237e0d04e40a36c97cd5dede67b
Source dataset
uspto-grants-1998_12
Patent number
US05854249

Reaction notes

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