Diisopropyl (S-(R*,R*))-tartrate → HCID 67252928, compound

HRID 2426802Notes

Reaction equation

HRID 2426802 reaction equation
C(O[CH:4](OCC)/[CH:5]=[CH:6]/[CH3:7])C.[C:11]([C@H:17]([C@@H:19]([C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22])[OH:20])[OH:18])([O:13][CH:14]([CH3:16])[CH3:15])=[O:12]>C1C=CC=CC=1.S(C1C=CC(C)=CC=1)([O-])(=O)=O.[NH+]1C=CC=CC=1>[CH:5](/[CH:4]1[O:20][C@H:19]([C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22])[C@@H:17]([C:11]([O:13][CH:14]([CH3:15])[CH3:16])=[O:12])[O:18]1)=[CH:6]\[CH3:7]

Participants

5

Reactant 2

HCID 112972Diisopropyl (S-(R*,R*))-tartrateHCID 6278424trans-2-Butenal diethyl acetal

Product 1

HCID 67252928HCID 67252928, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 241BenzeneSolvent

Procedure

A solution of (2E)-1,1-diethoxybut-2-ene (32.20 g, 223.27 mmol), (−)-diisopropyl D-tartrate (64.64 mL, 245.60 mmol) and pyridinium tosylate (2.24 g, 8.93 mmol) in 100 mL benzene was heated to 95° C. to distill off the solvent and EtOH produced. After 7 h at 95° C., the reaction was cooled to rt and concentrated in vacuo. Purification by normal phase chromatography (10->30% EtOAc/hexanes) yielded 35.37 g (55%) of diisopropyl (4S,5S)-2-[(1E)-prop-1-enyl]-1,3-dioxolane-4,5-dicarboxylate as an orange oil. 1H NMR (CDCl3, 400 MHz) 6.03 (m, 1H); 5.86 (m, 2H); 5.12 (m, 2H); 4.71 (d, J=3.84 Hz, 1H); 4.63 (d, J=3.84 Hz, 1H); 1.78 (m, 3H); 1.30 (d, J=6.23 Hz, 12H); LC/MS [M+H]+=287.

Workup

  1. distillationto distill off the solvent and EtOH
  2. customproduced
  3. concentrationconcentrated in vacuo
  4. customPurification by normal phase chromatography (10->30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d4968ab8bfaa4a02847075a3026e2749
Source dataset
uspto-grants-2011_06
Patent number
US07968571B2

Reaction notes

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