Dimethyl Sulfoxide → HCID 86607429, compound

HRID 1178560Notes

Reaction equation

HRID 1178560 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH:13]1[CH2:17][CH2:16][C:15](=[O:18])[N:14]1[CH2:19][CH2:20][CH2:21][C:22]1[S:26][C:25]([C:27]([O:29][CH3:30])=[O:28])=[CH:24][CH:23]=1.CCN(CC)CC>C(Cl)Cl>[CH:12]([CH:13]1[CH2:17][CH2:16][C:15](=[O:18])[N:14]1[CH2:19][CH2:20][CH2:21][C:22]1[S:26][C:25]([C:27]([O:29][CH3:30])=[O:28])=[CH:24][CH:23]=1)=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 69145264HCID 69145264, compound

Product 1

HCID 86607429HCID 86607429, compoundYield 98.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent5×

Conditions

Temperature
-78 °C

Procedure

A DCM solution of oxalyl chloride (4.38 mL, 2.0 M 8.76 mmol) was diluted with dry DCM (50 mL) and cooled to −78° C. then a solution of DMSO (0.76 mL, 10.77 mmol) in DCM (5 mL) was added dropwise. After 15 min., a solution of methyl 5-[3-(2-(hydroxymethyl)-5-oxopyrrolidin-1-yl)propyl]thiophene-2-carboxylate (2.0 g, 6.73 mmol) in DCM (10 mL) was added dropwise to this solution. The resulting solution was stirred at −78° C. for 2 hours. Et3N (4.7 mL, 33.65 mmol) was added and the solution warmed to RT. After 15 min. the solution was diluted with DCM (100 mL) and washed with a saturated solution of NH4Cl (2×100 mL), brine (100 mL), dried over sodium sulfate and concentrated in vacuo to afford the aldehyde intermediate (1.95 g, 98%) used in the next step without further purification.

Workup

  1. temperaturethe solution warmed to RT
  2. washwashed with a saturated solution of NH4Cl (2×100 mL), brine (100 mL)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8237fdbe820b4338a8b0a3eb07aeb066
Source dataset
uspto-grants-2007_10
Patent number
US07276531B2

Reaction notes

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