Dimethyl Sulfoxide → HCID 57699455, compound

HRID 1012937Notes

Reaction equation

HRID 1012937 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16](=[O:26])[NH:17][C@@H:18]1[CH2:23][CH2:22][C@@H:21]([CH2:24][OH:25])[O:20][CH2:19]1)([CH3:14])([CH3:13])[CH3:12].C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[C:11]([O:15][C:16](=[O:26])[NH:17][C@@H:18]1[CH2:23][CH2:22][C@@H:21]([CH:24]=[O:25])[O:20][CH2:19]1)([CH3:14])([CH3:12])[CH3:13]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 109880991,5-Anhydro-2,3,4-trideoxy-2-[[(1,1-diMethylethoxy)carbonyl]aMino]-D-erythrohexitol

Product 1

HCID 57699455HCID 57699455, compoundYield 84.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent4×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of oxalyl chloride (3.5 ml) in DCM (25 ml) cooled to −78° C., was added drop wise a solution of DMSO (3.5 ml) in DCM (25 ml). After 15 minutes stirring, a solution of (3R,6S)-(6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester (prepared as described in Eur. J. Org. Chem. (2003), 2418-2427; 3 g) in DCM (25 ml) was added drop wise. The reaction was stirred 1 h and a solution of triethylamine (15 ml) in DCM (15 ml) was added dropwise. The reaction proceeded for 1 hour, with warming to 0° C. Saturated sodium bicarbonate (50 ml) was added. The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was chromatographed (Hex/EtOAc 1:2) to afford the title aldehyde (2.5 g) as a colorless solid.

Workup

  1. stirringThe reaction was stirred 1 h
  2. waitThe reaction proceeded for 1 hour
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was chromatographed (Hex/EtOAc 1:2)

Sources & evidence

ORD record
ord-3cd5e2bd3ce2435e9ac91f4e66ba611e
Source dataset
uspto-grants-2011_07
Patent number
US07981886B2

Reaction notes

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