Sodium Azide → HCID 57827627, compound

HRID 1842152Notes

Reaction equation

HRID 1842152 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[C:5]([O:9][C:10]([N:12]([C:20]1[S:21][CH2:22][C@@H:23]2[CH2:28][CH2:27][CH2:26][C@:24]2([C:29]2[CH:34]=[C:33](B3OC(C)(C)C(C)(C)O3)[CH:32]=[C:31]([Cl:44])[CH:30]=2)[N:25]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:11])([CH3:8])([CH3:7])[CH3:6]>CO.[Cl-].[Na+].O.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:5]([O:9][C:10]([N:12]([C:20]1[S:21][CH2:22][C@@H:23]2[CH2:28][CH2:27][CH2:26][C@:24]2([C:29]2[CH:30]=[C:31]([Cl:44])[CH:32]=[C:33]([N:1]=[N+:2]=[N-:3])[CH:34]=2)[N:25]=1)[C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[O:11])([CH3:6])([CH3:7])[CH3:8]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 57827116HCID 57827116, compound

Product 1

HCID 57827627HCID 57827627, compoundYield 14%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Sodium azide (53 mg) and copper (II) acetate (19.9 mg) were added to a solution of (±)-N,N-bis(t-butoxycarbonyl){(4aR*,7aS*)-7a-[3-chloro-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-4,4a,5,6,7,7a-hexahydrocyclopenta[d][1,3]thiazin-2-yl}amine (1.16 g) in methanol (20 mL). The mixture was stirred at room temperature for six days. Brine was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (58.0 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-c81d620b38394ad9a99b373e533c719c
Source dataset
uspto-grants-2015_02
Patent number
US08946211B2

Reaction notes

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