10-Undecynoic acid → 10-Undecynoyl-OSu

HRID 1640369

Reaction equation

HRID 1640369 reaction equation
[C:1]([OH:13])(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11].[B-](F)(F)(F)F.CN(C(O[N:27]1[C:32](=[O:33])[CH2:31][CH2:30][C:28]1=[O:29])=[N+](C)C)C>CC#N>[C:28]1(=[O:29])[N:27]([O:12][C:1](=[O:13])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]#[CH:11])[C:32](=[O:33])[CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 3103910-Undecynoic acidHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborate

Product 1

HCID 8713085610-Undecynoyl-OSu

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 10-undecynoic acid (0.40 g, 2.2 mmol) in CH3CN (10 mL) was added O—(N-succinimidyl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.99 g, 3.29 mmol). After stirring for 2 min at RT, the reaction was quenched with 1% AcOH and diluted with CHCl3 (150 mL). The organic solution was then extracted with 1% AcOH (10 mL), rinsed with H2O (2×40 mL), then dried over Na2SO4. The solution was then decanted and concentrated. A quantitative yield was assumed and the material was taken on directly to the next step. TLC (10% MeOH/CHCl3) Rf=0.90, UV active.

Workup

  1. customthe reaction was quenched with 1% AcOH
  2. additiondiluted with CHCl3 (150 mL)
  3. extractionThe organic solution was then extracted with 1% AcOH (10 mL)
  4. washrinsed with H2O (2×40 mL)
  5. dry with materialdried over Na2SO4
  6. customThe solution was then decanted
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b57f550802c247009fc8c1305231d8b4
Source dataset
uspto-grants-2012_02
Patent number
US08114636B2

Linked notes

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