Pyridine → HCID 59611511, compound

HRID 2039212Notes

Reaction equation

HRID 2039212 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-ab943dde42ac489e993c0b0000b6dab0
Source dataset
uspto-grants-2013_11
Patent number
US08575118B2

Reaction notes

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