Dimethyl Sulfoxide → HCID 18187475, compound

HRID 1357951Notes

Reaction equation

HRID 1357951 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([CH:24]([OH:31])[CH:25]([CH3:30])[C:26](=[O:29])[CH2:27][CH3:28])[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(N(CC)C(C)C)(C)C>C(Cl)Cl>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([C:24](=[O:31])[CH:25]([CH3:30])[C:26](=[O:29])[CH2:27][CH3:28])[CH2:20][CH2:19]1)=[O:17])([CH3:13])([CH3:12])[CH3:14]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 18187644HCID 18187644, compound

Product 1

HCID 18187475HCID 18187475, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of oxalyl chloride (0.34 mL, 3.9 mmol) in methylene chloride (12 mL) at −78° C. was treated with DMSO (0.43 mL, 6.0 mmol) and the resulting mixture was stirred cold for 10 min. A solution of 1-(t-butoxycarbonyl)-4-(1-(RS)-hydroxy-2-(RS)-methyl-3-oxopent-1-yl)piperidine (514 mg, 1.7 mmol) (from Step C) was added and the resulting solution was stirred cold for 1 h. N,N-Diisopropylethylamine (2.4 mL, 13.7 mmol) was added and the resulting mixture was warmed to 0° C. The reaction was quenched with 1.0 N HCl (25 mL) and extracted with ether (100 mL). The extract was dried over magnesium sulfate and concentrated. MPLC (Biotage) on a 40S silica cartridge using 2:1 v/v hexanes/ethyl acetate as the eluent afforded 435 mg (85%) of the title compound.

Workup

  1. stirringthe resulting solution was stirred cold for 1 h
  2. customThe reaction was quenched with 1.0 N HCl (25 mL)
  3. extractionextracted with ether (100 mL)
  4. dry with materialThe extract was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-84f35877d27c46caaf6888983545875d
Source dataset
uspto-grants-2003_07
Patent number
US06593346B2

Reaction notes

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