Pyridine → HCID 58136204, compound

HRID 1161920Notes

Reaction equation

HRID 1161920 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-0acffb2e24d5473bb23f9bd758dc271c
Source dataset
uspto-grants-2010_10
Patent number
US07820660B2

Reaction notes

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