3,4-dihydro-2H-pyran → HCID 86742225, compound

HRID 580025Notes

Reaction equation

HRID 580025 reaction equation
[OH:1][CH:2]([C@H:4]1[CH:7]([S:8][C:9]([S:11][CH2:12][S:13][CH3:14])=[S:10])[NH:6][C:5]1=[O:15])[CH3:3].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:33]1[CH:38]=[CH:37][CH2:36][CH2:35][CH2:34]1>C(Cl)Cl>[O:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH:34]1[O:1][CH:2]([C@H:4]1[CH:7]([S:8][C:9]([S:11][CH2:12][S:13][CH3:14])=[S:10])[NH:6][C:5]1=[O:15])[CH3:3]

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22838541HCID 22838541, compound

Product 1

HCID 86742225HCID 86742225, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

To a stirred solution of 2.67 g (10 mmole) 3-(R)-(1-hydroxyethyl)-4-(methylthiomethylthio[thiocarbonyl]thio)-2-azetidinone in 30 ml methylene chloride at room temperature is added 0.8 g pyridinium p-toluenesulfonate and 1.26 g (15 mmole) dihydropyran and the mixture is stirred at 30° C. for five hours. The solvent is evaporated in vacuo, the residual oil is dissolved in ethyl ether, washed with brine, water, dried (Na2SO4) and concentrated in vacuo to afford the title compound. B. A solution of 3.51 g (10 mmole) of the product of Part A, above, and 4.0 g (20 mmole) t-butoxycarbonyloxymethyl glyoxylate in 150 ml benzene is heated at reflux overnight while removing water in a Dean-Stark trap. The resulting product is isolated and purified as described in Example 4 to obtain the desired 2-hydroxyacetate.

Workup

  1. customThe solvent is evaporated in vacuo
  2. dissolutionthe residual oil is dissolved in ethyl ether
  3. washwashed with brine, water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b7d299a184fb42fe95fbeb8d2e0bc2e6
Source dataset
uspto-grants-1988_06
Patent number
US04751297

Reaction notes

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