Pyridine → HCID 58136204, compound

HRID 2114779Notes

Reaction equation

HRID 2114779 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][C@@H:17]([F:19])[CH2:16][C@H:12]1[C:13](O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N:20]1C=CC=CC=1.CC(OC(OC(OC(C)(C)C)=O)=O)(C)C.C(=O)(O)[O-].[NH4+]>O1CCOCC1>[CH2:1]([O:8][C:9]([N:11]1[CH2:18][C@@H:17]([F:19])[CH2:16][C@H:12]1[C:13]([NH2:20])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 90495Di-tert-butyl dicarbonateHCID 11708768HCID 11708768, compound

Product 1

HCID 58136204HCID 58136204, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A stirred solution of (4S)-1-[(Benzyloxy)carbonyl]-4-fluoro-L-proline in dioxane was treated with pyridine (0.7 eq.) and Boc2O (1.3 eq.), then ammonium bicarbonate (1.26 eq.) was added and the mixture was stirred at room temperature for 15 hours. Dioxane was concentrated and the residue was taken up in ethyl acetate, washed with 1 N HCl and brine, dried over Na2SO4 to give, after filtration and concentration, title compound.

Workup

  1. concentrationDioxane was concentrated
  2. washwashed with 1 N HCl and brine
  3. dry with materialdried over Na2SO4
  4. customto give
  5. filtrationafter filtration and concentration, title compound

Sources & evidence

ORD record
ord-1c21b9ce9b254262ba465c58009989af
Source dataset
uspto-grants-2008_10
Patent number
US07435734B2

Reaction notes

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