Dimethyl Sulfoxide → HCID 89397317, compound

HRID 2171596Notes

Reaction equation

HRID 2171596 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Si:11]([O:18][C@H:19]1[CH2:23][CH2:22][N:21](/[N:24]=[CH:25]/[C:26]2[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[C:28]([Cl:34])[C:27]=2[CH3:35])[C@@H:20]1[CH2:36][OH:37])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]>C(Cl)Cl>[Si:11]([O:18][C@H:19]1[CH2:23][CH2:22][N:21](/[N:24]=[CH:25]/[C:26]2[CH:33]=[CH:32][C:29]([C:30]#[N:31])=[C:28]([Cl:34])[C:27]=2[CH3:35])[C@@H:20]1[CH:36]=[O:37])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 134951165HCID 134951165, compound

Product 1

HCID 89397317HCID 89397317, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of oxalyl chloride (1.92 mL, 0.022 moles) in dry DCM (25 mL) at −78° C. was added DMSO (3.12 mL, 0.044 moles) and stirred for 30 min. Then to the reaction mixture at the same temperature was added a solution of 4-((E)-((2R,3S)-3-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)pyrrolidin-1-ylimino)methyl)-2-chloro-3-methylbenzonitrile (IVa) (7.5 g, 0.0184 moles) in 100 mL DCM and continued stirring for 1 h. The reaction mixture was quenched with triethylamine (13 mL) at −30° C. and stirred for 1 h. Then it was diluted with DCM and washed with water, brine, dried over Na2SO4 and concentrated to get the title compound which was used in the next step without further purification.

Workup

  1. stirringcontinued stirring for 1 h
  2. customThe reaction mixture was quenched with triethylamine (13 mL) at −30° C.
  3. stirringstirred for 1 h
  4. additionThen it was diluted with DCM
  5. washwashed with water, brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-397aaa386d3e458bb8c02e92e2073f4e
Source dataset
uspto-grants-2015_06
Patent number
US09051326B2

Reaction notes

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