Dimethyl Sulfoxide → HCID 131728829, compound

HRID 547792Notes

Reaction equation

HRID 547792 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]([F:55])([F:54])[C:13]1[CH:14]=[C:15]([C:23]([CH3:53])([CH3:52])[C:24]([N:26]([CH3:51])[C:27]2[C:28]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=3[CH3:50])=[CH:29][C:30]([N:33]3[CH2:37][C@H:36]([OH:38])[CH2:35][C@H:34]3[CH2:39][O:40][C:41](=[O:43])[CH3:42])=[N:31][CH:32]=2)=[O:25])[CH:16]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:18]=1.C(N(CC)C(C)C)(C)C>ClCCl.COC(C)(C)C>[F:22][C:19]([F:20])([F:21])[C:17]1[CH:16]=[C:15]([C:23]([CH3:52])([CH3:53])[C:24]([N:26]([CH3:51])[C:27]2[C:28]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=3[CH3:50])=[CH:29][C:30]([N:33]3[CH2:37][C:36](=[O:38])[CH2:35][C@H:34]3[CH2:39][O:40][C:41](=[O:43])[CH3:42])=[N:31][CH:32]=2)=[O:25])[CH:14]=[C:13]([C:12]([F:55])([F:54])[F:11])[CH:18]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 131728828HCID 131728828, compound

Product 1

HCID 131728829HCID 131728829, compoundYield 94.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 0.08 ml (0.9 mmol) oxalyl chloride in 2 ml dichloromethane were added dropwise at −78° C. 0.13 ml (1.9 mmol) dimethyl sulfoxide and after a period of 3 min. a solution of 0.50 g (0.78 mmol) (2S,4R)-acetic acid 1-(5-{[2-(3,5-bis-trifluoromethyl-phenyl)-2-methyl-propionyl]-methyl-amino}-4-o-tolyl-pyridin-2-yl)-4-hydroxy-pyrrolidin-2-ylmethyl ester in 2 ml dichloromethane. After stirring at −78° C. for 30 min. 0.7 ml (4 mmol) N,N-diisopropylethylamine were added. The reaction mixture was allowed to warm to room temperature during 1 h, diluted with tert-butyl methyl ether and washed with an aqueous ammonium chloride solution. The aqueous layer was extracted with two portions of tert-butyl methyl ether. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 0.47 g (94%) of the title compound as a white solid.

Workup

  1. temperatureto warm to room temperature during 1 h
  2. washwashed with an aqueous ammonium chloride solution
  3. extractionThe aqueous layer was extracted with two portions of tert-butyl methyl ether
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92d8a67fa5ed4e979fb6f4fc090a2a9a
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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