2,2-Dimethoxypropane → HCID 15343999, compound

HRID 1078089Notes

Reaction equation

HRID 1078089 reaction equation
[CH3:1][C:2]([CH3:23])([O:4][C:5]([NH:7][CH:8]([CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH:9]([C:11]1[O:12][CH:13]=[CH:14][CH:15]=1)[OH:10])=[O:6])[CH3:3].CO[C:26](OC)([CH3:28])[CH3:27].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH:17]1([CH2:16][C@H:8]2[C@H:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[O:10][C:26]([CH3:28])([CH3:27])[N:7]2[C:5]([O:4][C:2]([CH3:23])([CH3:1])[CH3:3])=[O:6])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 4

HCID 64952,2-Dimethoxypropane2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)2×HCID 516892Sodium BicarbonateHCID 19378604HCID 19378604, compound

Product 1

HCID 15343999HCID 15343999, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[R-(R*,S*)]-β-[[(1,1-Dimethylethoxy)carbonyl]amino]-α-(2-furanyl)cyclohexanepropanol (41.63 g., 128.9 mmole, 1 eq.) was dissolved in distilled dichloromethane (1 l., 0.129M) under an argon atmosphere. 2,2-Dimethoxypropane (158.5 ml., 1289 mmole, 10 eq.) was added. The solution was cooled in an ice bath and pyridinium toluene-4-sulfonate (3.24 g., 12.89 mmole, 0.1 eq.) was added. The cooling bath was removed and the mixture was stirred at room temperature for 24 hours. Additional 2,2-dimethoxypropane (50 ml., 407 mmole, 3.2 eq.) and pyridinium toluene-4-sulfonate (1.5 g., 6.0 mmole, 0.05 eq.) were added and stirring at room temperature was continued for 20 hours. Solid sodium bicarbonate was added and the solvent was removed in vacuo. The residue was dissolved in ether (1 l.) and washed with saturated sodium bicarbonate solution (300 ml.) and saturated sodium chloride solution (300 ml.), dried (MgSO4) and freed of solvent in vacuo leaving a yellow oil (47.04 g.). This was chromatographed on silica gel (Merck, 1300 g.) eluting with ether:hexane (1:9) to give (4S-trans)-4-(cyclohexylmethyl)-5-(2-furanyl)-2,2-dimethyl-3-oxazolidinecarboxylic acid, 1,1-dimethylethyl ester as a colorless oil which crystallized on standing (36.66 g., 78.3%), m.p. 52°-56°. [α]D =-46.9° (c=1.6, methanol). TLC (silica gel, 1:3, ether:hexane) Rf =0.58.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customThe cooling bath was removed
  3. stirringstirring at room temperature
  4. waitwas continued for 20 hours
  5. customthe solvent was removed in vacuo
  6. dissolutionThe residue was dissolved in ether (1 l.)
  7. washwashed with saturated sodium bicarbonate solution (300 ml.) and saturated sodium chloride solution (300 ml.)
  8. dry with materialdried (MgSO4)
  9. customleaving a yellow oil (47.04 g.)
  10. customThis was chromatographed on silica gel (Merck, 1300 g.)
  11. washeluting with ether:hexane (1:9)

Sources & evidence

ORD record
ord-20cc377dc1fb4928bfb1913fd3e95ac6
Source dataset
uspto-grants-1996_08
Patent number
US05545838

Reaction notes

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