Di-tert-butyl dicarbonate → Di-tert-butyl (3-(3-(4-((pyridin-2-yloxy)methyl)benzyl)isoxazol-5-yl)pyridin-2-yl)imidodicarbonate

HRID 557272Notes

Reaction equation

HRID 557272 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]#[CH:23])=[CH:20][CH:19]=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+:24]([CH2:27][CH2:28][C:29]1[CH:42]=[CH:41][C:32]([CH2:33][O:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=2)=[CH:31][CH:30]=1)([O-])=[O:25].C(OC(OC(C)(C)C)=O)(OC(C)(C)C)=O>O1CCCC1>[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([C:22]2[O:25][N:24]=[C:27]([CH2:28][C:29]3[CH:30]=[CH:31][C:32]([CH2:33][O:34][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][N:36]=4)=[CH:41][CH:42]=3)[CH:23]=2)=[CH:20][CH:19]=[CH:18][N:17]=1)[C:9]([O:11][C:12]([CH3:14])([CH3:15])[CH3:13])=[O:10])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 580762662-((4-(2-Nitroethyl)benzyl)oxy)pyridineHCID 59841574tert-butyl N-[(tert-butoxy)carbonyl]-N-(3-ethynylpyridin-2-yl)carbamate

Product 1

HCID 25114167Di-tert-butyl (3-(3-(4-((pyridin-2-yloxy)methyl)benzyl)isoxazol-5-yl)pyridin-2-yl)imidodicarbonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under stirring at room temperature, to a solution of di-tert-butyl(3-ethinyl pyridin-2-yl)imidodicarbonate described in Preparation Example 3-1-1 (12 g), 2-(4-(2-nitro-ethyl)-benzyloxy)pyridine described in Preparation Example 1-3-4 (19.4 g), 4-dimethyl aminopyridine (230 mg), tetrahydrofuran (200 mL) was added di-tert-butyl dicarbonate (28.8 g) divided into four portions over 8 hours. After the additions were finished, stirring was carried out at room temperature for an additional 22 hours. Silica gel was added to the reaction solution and the solvent was concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (heptane:ethyl acetate=3:1 then 2:1) to obtain the title compound (11.8 g, containing approximately 70% of the target compound).

Workup

  1. waitwas carried out at room temperature for an additional 22 hours
  2. additionSilica gel was added to the reaction solution
  3. concentrationthe solvent was concentrated under a reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (heptane
  5. customethyl acetate=3:1 then 2:1) to obtain

Sources & evidence

ORD record
ord-269ae8a8c00242258a64302cb6128487
Source dataset
uspto-grants-2011_11
Patent number
US08058444B2

Reaction notes

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