(Diethylamino)sulfur trifluoride → HCID 131728830, compound

HRID 1951702Notes

Reaction equation

HRID 1951702 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-90b78853427c48308620cff697c2f3df
Source dataset
uspto-grants-2013_03
Patent number
US08404708B2

Reaction notes

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