1,4-Dioxane hydrochloride → HCID 86700682, compound

HRID 1406864Notes

Reaction equation

HRID 1406864 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([N:18]3[CH2:23][CH2:22][CH:21]([C:24]4[O:28][N:27]=[C:26]([C@@H:29]5[CH2:34][CH2:33][C@@H:32]([N:35]([O:39][CH2:40][C:41]6[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=6)[C:36]([Cl:38])=[O:37])[CH2:31][N:30]5C(OC(C)(C)C)=O)[N:25]=4)[CH2:20][CH2:19]3)=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl.O1CCOCC1>>[CH2:40]([O:39][N:35]([C:36]([Cl:38])=[O:37])[C@H:32]1[CH2:31][NH:30][C@H:29]([C:26]2[N:25]=[C:24]([CH:21]3[CH2:22][CH2:23][N:18]([C:16]([O:15][CH2:14][CH:12]4[C:11]5[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=5[C:5]5[C:13]4=[CH:1][CH:2]=[CH:3][CH:4]=5)=[O:17])[CH2:19][CH2:20]3)[O:28][N:27]=2)[CH2:34][CH2:33]1)[C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1

Participants

3

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 86700680HCID 86700680, compound

Product 1

HCID 86700682HCID 86700682, compoundYield 115.6%

Procedure

A mixture of (2S,5R)-tert-butyl 2-(5-(1-(((9H-fluoren-9-yl)methoxy)carbonyl)piperidin-4-yl)-1,2,4-oxadiazol-3-yl)-5-(benzyloxy(chlorocarbonyl)amino)piperidine-1-carboxylate (˜400 mg) and 4 N HCl/dioxane (5.0 mL) was stirred at rt for 2 hrs. The solvent was then removed under vacuum to give (9H-fluoren-9-yl)methyl 4-(3-((2S,5R)-5-(benzyloxy(chlorocarbonyl)amino)piperidin-2-yl)-1,2,4-oxadiazol-5-yl)piperidine-1-carboxylate (400 mg) as a white solid. ESI-MS (EI+, m/z): 642 [M+H]+.

Workup

  1. customThe solvent was then removed under vacuum

Sources & evidence

ORD record
ord-d943c621dcc94850a6b696bbd9d8620e
Source dataset
uspto-grants-2014_12
Patent number
US08916709B2

Reaction notes

Loading…