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

HRID 1891521Notes

Reaction equation

HRID 1891521 reaction equation
[C:1]([C:3]1[C:4]([N:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[N:5][CH:6]=[CH:7][CH:8]=1)#[CH: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>CN(C)C1C=CN=CC=1.O1CCCC1>[N:36]1[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=1[O:34][CH2:33][C:32]1[CH:41]=[CH:42][C:29]([CH2:28][C:27]2[CH:2]=[C:1]([C:3]3[C:4]([N:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[N:5][CH:6]=[CH:7][CH:8]=3)[O:25][N:24]=2)=[CH:30][CH:31]=1

Participants

6

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)imidodicarbonateYield 70%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of di-tert-butyl (3-ethynylpyridin-2-yl)imidodicarbonate (12 g) described in Manufacturing Example 2-4-1, 2-(4-(2-nitro-ethyl)-benzyloxy)pyridine (19.4 g) described in Manufacturing Example 2-1-4, 4-dimethylaminopyridine (230 mg) and tetrahydrofuran (200 mL) was added di-tert-butyl dicarbonate (28.8 g) in 4 portions over the course of 8 hours at room temperature with stirring. After addition was complete, this was stirred at room temperature for a further 22 hours. Silica gel was added to the reaction solution, and the solvent was concentrated under a reduced pressure. The resulting silica gel was purified by silica gel chromatography (heptane:ethyl acetate=3:1 then 2:1) to obtain an oily product (11.8 g, containing about 70% of title compound) containing the title compound.

Workup

  1. additionAfter addition
  2. stirringthis was stirred at room temperature for a further 22 hours
  3. additionSilica gel was added to the reaction solution
  4. concentrationthe solvent was concentrated under a reduced pressure
  5. customThe resulting silica gel was purified by silica gel chromatography (heptane
  6. customethyl acetate=3:1 then 2:1) to obtain

Sources & evidence

ORD record
ord-bcf2fa25314c42249ee76b105c5cf370
Source dataset
uspto-grants-2013_08
Patent number
US08507530B2

Reaction notes

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