(Diethylamino)sulfur trifluoride → HCID 131728830, compound

HRID 547794Notes

Reaction equation

HRID 547794 reaction equation
[F:1][C:2]([F:45])([F:44])[C:3]1[CH:4]=[C:5]([C:13]([CH3:43])([CH3:42])[C:14]([N:16]([CH3:41])[C:17]2[C:18]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])=[CH:19][C:20]([N:23]3[CH2:27][C@H:26](O)[CH2:25][C@H:24]3[CH2:29][O:30][C:31](=[O:33])[CH3:32])=[N:21][CH:22]=2)=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.C(N(S(F)(F)[F:52])CC)C>ClCCl.[OH-].[Na+]>[F:11][C:9]([F:10])([F:12])[C:7]1[CH:6]=[C:5]([C:13]([CH3:43])([CH3:42])[C:14]([N:16]([CH3:41])[C:17]2[C:18]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[CH3:40])=[CH:19][C:20]([N:23]3[CH2:27][C@@H:26]([F:52])[CH2:25][C@H:24]3[CH2:29][O:30][C:31](=[O:33])[CH3:32])=[N:21][CH:22]=2)=[O:15])[CH:4]=[C:3]([C:2]([F:1])([F:44])[F:45])[CH:8]=1

Participants

5

Reactant 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 131728828HCID 131728828, compound

Product 1

HCID 131728830HCID 131728830, compoundYield 36.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 0.14 g (0.21 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 were added dropwise at 0° C. 0.03 ml (0.2 mmol) (diethylamino)sulfur trifluoride. After 1 h the reaction mixture was diluted with a 0.5 M aqueous sodium hydroxide solution and extracted with four portions of dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Flash column chromatography gave 47 mg (35%) of the title compound as a white solid.

Workup

  1. extractionextracted with four portions of dichloromethane
  2. dry with materialThe combined organic extracts were dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-519c3e594c8442dc909712598e2a2ca0
Source dataset
uspto-grants-2011_05
Patent number
US07939533B2

Reaction notes

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