Pyridine → HCID 117717655, compound

HRID 592054Notes

Reaction equation

HRID 592054 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C@@H:14]2[O:15][C@@H:11]([CH2:12][CH2:13]2)[C@@H:10]1[C:16]([OH:18])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:19]1C=CC=CC=1.O(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O>O1CCOCC1>[C:16]([C@H:10]1[C@H:11]2[O:15][C@H:14]([CH2:13][CH2:12]2)[C@H:9]1[NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])(=[O:18])[NH2:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 90495Di-tert-butyl dicarbonateHCID 89738579HCID 89738579, compound

Product 1

HCID 117717655HCID 117717655, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(1S,2R,3S,4R)-3-(tert-butoxycarbonylamino)-7-oxabicyclo[2.2.1]heptane-2-carboxylic acid (13) (44 mg, 0.17 mmol) was taken in dioxane when pyridine (1.7 eq) was added followed by addition of BOC2O. The reaction mixture was stirred at rt for 40 min when NH4CO3 (38 mg, 0.49 mmol) was added and the reaction mixture was stirred at rt for 15 h when TLC confirmed formation of product. The reaction mixture was concentrated and purified by column chromatography using silica gel (100-200 mesh) to afford the desired product (43 mg, 95%) as a yellow oil.

Workup

  1. additionwas added
  2. additionwas added
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-63476d7664c644079bf401444660bb95
Source dataset
uspto-grants-2016_01
Patent number
US09238656B2

Reaction notes

Loading…