Water → Ethyl (1S,3R,4S)-4-azido-3-[(tert-butoxycarbonyl)amino]cyclohexane-1-carboxylate

HRID 2360994Notes

Reaction equation

[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:9][C:10]([NH:12][C@H:13]1[C@H:18](OS(C)(=O)=O)[CH2:17][CH2:16][C@H:15]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:14]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].O.C(OCC)(=O)C>[Cl-].C[N+](C)(C)C.CN1CCCC1=O>[N:1]([C@H:18]1[CH2:17][CH2:16][C@H:15]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:14][C@H:13]1[NH:12][C:10]([O:9][C:5]([CH3:6])([CH3:8])[CH3:7])=[O:11])=[N+:2]=[N-:3]

Participants

Conditions

Temperature: 60 °C

Procedure

Sodium azide (357.6 mg) and tetramethylammonium chloride (91.0 mg) were added at room temperature to a solution (2 mL) of ethyl (1S,3R,4R)-3-[(t-butoxycarbonyl)amino]-4-methanesulfonyloxycyclohexanecarboxylate (1.01 g) in N-methyl-2-pyrrolidone, followed by stirred at 60° C. for 74 hours. Water and ethyl acetate were added to the reaction mixture, and the organic layer was washed with aqueous saturated sodium bicarbonate solution and water, followed by drying over magnesium sulfate anhydrate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography (n-hexane:ethyl acetate=4:1), to thereby yield 648.3 mg of the title compound. Spectral data of this compound were found to be identical with those of the compound of Example 5.

Workup

washthe organic layer was washed with aqueous saturated sodium bicarbonate solution and water
dry with materialby drying over magnesium sulfate anhydrate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-78d37fe6c10642f0a45635be8641753d
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08686189B2

Reaction notes

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