Dimethyl Sulfoxide → HCID 57163548, compound

HRID 613704Notes

Reaction equation

HRID 613704 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:14][C:15]([NH:17][C@H:18]([CH2:28][OH:29])[CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:16])[CH:12]=[CH2:13].C(N(C(C)C)CC)(C)C>C(Cl)Cl.CCOC(C)=O>[CH2:11]([O:14][C:15]([NH:17][C@H:18]([CH:28]=[O:29])[CH2:19][CH2:20][C:21]([O:23][C:24]([CH3:26])([CH3:25])[CH3:27])=[O:22])=[O:16])[CH:12]=[CH2:13]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 57121346HCID 57121346, compound

Product 1

HCID 57163548HCID 57163548, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-70 °C

Procedure

To a solution of DMSO (1.51 g, 19.3 mmol) in CH2Cl2 (25 ml) at -70° C. was added oxalyl chloride (1.34 g, 19.3 mmol). After 10 minutes at -70° C., a solution of (206a) (2.4 g, 8.8 mmol) in CH2Cl2 (10 ml) was added dropwise and the mixture stirred for 15 minutes at -70° C. Diisopropylethylamine (3.4 g, 26.3 mmol) was added and the mixture stirred at -25° C. for 15 minutes then diluting with EtOAc (50 ml) washed with a solution of sodium hydrogensulfate 2M, concentrated to give an oil which was used immediately without purification: 1H NMR (CDCl3) δ 9.5 (1H, s), 6.0-5.5 (2H, m), 5.5-5.1 (2H, m), 4.5 (2H, m), 4.2 (1H, m), 2.4-2.10 (2H, m), 2.05 (2H, m), 1.36 (9H, s).

Workup

  1. stirringthe mixture stirred at -25° C. for 15 minutes
  2. washwashed with a solution of sodium hydrogensulfate 2M
  3. concentrationconcentrated
  4. customto give an oil which
  5. customwas used immediately without purification

Sources & evidence

ORD record
ord-7a235e2d956644ba960731f16e30fe51
Source dataset
uspto-grants-1999_12
Patent number
US06008217

Reaction notes

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