Hydrochloric Acid → HCID 86700675, compound

HRID 1406860Notes

Reaction equation

HRID 1406860 reaction equation
[CH2:1]([O:8][N:9]([C:28]([Cl:30])=[O:29])[C@H:10]1[CH2:15][N:14](C(OC(C)(C)C)=O)[C@H:13]([C:23]2[N:27]=[CH:26][O:25][N:24]=2)[CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCOCC1>[O:25]1[CH:26]=[N:27][C:23]([C@H:13]2[NH:14][CH2:15][C@H:10]([N:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:28]([Cl:30])=[O:29])[CH2:11][CH2:12]2)=[N:24]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86700674HCID 86700674, compound

Product 1

HCID 86700675HCID 86700675, compoundYield 113.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of (2S,5R)-tert-butyl 5-(benzyloxy(chlorocarbonyl)amino)-2-(1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate (1.6 g), and 4 N HCl in dioxane (18 mL), was stirred at rt for 2 hrs. The solvent was then removed under vacuum to give (3R,6S)-6-(1,2,4-oxadiazol-3-yl)piperidin-3-yl(benzyloxy)carbamic chloride (1.4 g) as a white solid, which was used directly in the next step. ESI-MS (EI+, m/z): 301.0.

Workup

  1. customThe solvent was then removed under vacuum

Sources & evidence

ORD record
ord-4fd5253f9c614fb5b0e7183e3ac72c96
Source dataset
uspto-grants-2014_12
Patent number
US08916709B2

Reaction notes

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