alpha Lipoic acid → HCID 11142791, compound

HRID 1857934Notes

Reaction equation

HRID 1857934 reaction equation
OC1C2N=NNC=2C=CC=1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[O:42]1[CH2:47][CH2:46][N:45]([CH2:48][CH2:49][NH2:50])[CH2:44][CH2:43]1.[CH2:51]1[CH:55]([CH2:56][CH2:57][CH2:58][CH2:59][C:60](O)=[O:61])[S:54][S:53][CH2:52]1>O1CCCC1>[S:53]1[CH2:52][CH2:51][CH:55]([CH2:56][CH2:57][CH2:58][CH2:59][C:60]([NH:50][CH2:49][CH2:48][N:45]2[CH2:46][CH2:47][O:42][CH2:43][CH2:44]2)=[O:61])[S:54]1

Participants

7

Reactant 5

HCID 864alpha Lipoic acidHCID 81531DiisopropylethylamineHCID 4082852-MorpholinoethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178418300HCID 178418300, compound

Product 1

HCID 11142791HCID 11142791, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.5 g of hydroxybenzotriazole, 10.5 g of 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate, 7.8 g of diisopropylethylamine and 3.9 g of 2-morpholino-1-ethylamine are added at room temperature to a solution of 6.2 g of thioctic acid in 180 ml of tetrahydrofuran. After 20 hours, the reaction mixture is concentrated under reduced pressure. The residue is taken up in ethyl acetate, washed and then dried over Na2SO4. Concentration under reduced pressure yields 8.4 g of the expected product.

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. washwashed
  3. dry with materialdried over Na2SO4
  4. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-453e945660ad4ef99d2a399d5e1c4bc7
Source dataset
uspto-grants-2000_11
Patent number
US06150358

Reaction notes

Loading…