Dimethyl Sulfoxide → HCID 58746799, compound

HRID 724650Notes

Reaction equation

HRID 724650 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([N:15]1[C:19](=[O:20])[CH2:18][CH:17]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][C:28]3([CH2:34][OH:35])[CH2:32][CH2:31][C:30](=[O:33])[NH:29]3)=[CH:23][CH:22]=2)[S:16]1(=[O:37])=[O:36])([CH3:14])([CH3:13])[CH3:12].C(N(CC)C(C)C)(C)C>C(Cl)Cl.O>[C:11]([N:15]1[C:19](=[O:20])[CH2:18][CH:17]([C:21]2[CH:26]=[CH:25][C:24]([CH2:27][C:28]3([CH:34]=[O:35])[CH2:32][CH2:31][C:30](=[O:33])[NH:29]3)=[CH:23][CH:22]=2)[S:16]1(=[O:36])=[O:37])([CH3:14])([CH3:12])[CH3:13]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 21879105HCID 21879105, compound

Product 1

HCID 58746799HCID 58746799, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Oxalyl chloride (74.3 μL, 0.878 mmol) was stirred in methylene chloride (2.6 mL), and the resulting solution was cooled to −78° C., whereupon dimethyl sulfoxide (142 μL, 2.00 mmol) was added. Then to the mixture, a solution of 2-tert-butyl-5-(4-[2-(hydroxymethyl)-5-oxopyrrolidin-2-yl]methylphenyl)isothiazolidin-3-one 1,1-dioxide (105 mg, 0.266 mmol) in dichloromethane (2.0 mL) was added dropwise, within five minutes. The mixture was stirred for fifteen minutes at −78° C.; after addition of N,N-diisopropylethylamine (695 μL, 3.99 mmol) the mixture was allowed to reach room temperature, and poured into water (1 mL). The aqueous phase was extracted twice with dichloromethane (5 mL) and the combined extracts were evaporated to give the crude aldehyde as a yellow oil. Purification on the preparative LCMS gave the desired aldehyde as a tan solid (30 mg, 30%). 1H NMR (400 MHz, CDCl3): δ 9.60 (s, 1H), 7.38 (m, 2H), 7.25 (m, 2H), 6.70 (s, 1H), 4.76 (m, 1H), 3.17 (m, 1H), 2.92 (m, 1H), 2.30 (m, 2H), 2.18 (m, 2H), 1.65 (s, 9H); LCMS found for C19H25N2O5S (M+H)+: m/z=393

Workup

  1. additionwas added
  2. customto reach room temperature
  3. extractionThe aqueous phase was extracted twice with dichloromethane (5 mL)
  4. customthe combined extracts were evaporated
  5. customto give the crude aldehyde as a yellow oil
  6. customPurification on the preparative LCMS

Sources & evidence

ORD record
ord-ea80a93802b9488caa55b29d12291a31
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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