Pyridine → HCID 59611511, compound

HRID 71966Notes

Reaction equation

HRID 71966 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:20][CH2:21][OH:22])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].F[B-](F)(F)F.[S:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[S:30][CH+:29]1.N1C=CC=CC=1.C(N(CC)CC)C>ClCCl>[S:28]1[C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=2[S:30][CH:29]1[O:22][CH2:21][CH2:20][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:10]([O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:11]

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 13970788Boc-L-Homoser-ObzlHCID 178505383HCID 178505383, compound

Product 1

HCID 59611511HCID 59611511, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(S)-Benzyl 2-(tert-butoxycarbonylamino)-4-hydroxybutanoate (5.76 g, 18.62 mmol) and 1,3-benzodithiol-2-ylium tetrafluoroborate (4.69 g, 19.55 mmol) were dissolved in dichloromethane (186 mL) and pyridine (4.42 g, 55.86 mmol) was added at room temperature. The mixture was stirred overnight. Upon completion of the reaction, it was quenched with triethylamine (11.5 g, 113.5 mmol) and diluted with dichloromethane. The organic layer was then washed with saturated NaHCO3 and brine. The organic layer was dried over MgSO4 and concentrated down in vacuo. The residue was then purified on normal phase column to obtain a clear oil. 7.6 g (88%).

Workup

  1. customUpon completion of the reaction, it
  2. washThe organic layer was then washed with saturated NaHCO3 and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated down in vacuo
  5. customThe residue was then purified on normal phase column
  6. customto obtain a clear oil

Sources & evidence

ORD record
ord-d117d1230655483a9ca26ca01fe31026
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

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