Diisopropyl Ether → HCID 9865778, compound

HRID 1180119Notes

Reaction equation

HRID 1180119 reaction equation
[F:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:15])[CH2:8][NH:9][C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])[C@H:4]([C:16]#[N:17])[CH2:3]1.O.[C:19]1([S:25]([OH:28])(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(OC(C)C)(C)C>CO>[C:19]1([S:25]([OH:28])(=[O:27])=[O:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[F:1][C@@H:2]1[CH2:6][N:5]([C:7](=[O:15])[CH2:8][NH:9][C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])[C@H:4]([C:16]#[N:17])[CH2:3]1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 9865779HCID 9865779, compoundHCID 15619088Hydroxybenzenesulfonic acid

Product 1

HCID 9865778HCID 9865778, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

(2S,4S)-4-Fluoro-1-{[(2-hydroxy-1,1-dimethylethyl)amino]acetyl}pyrrolidine-2-carbonitrile (222 g) was suspended in methanol (3330 mL). While stirring this suspension at room temperature, a methanol solution of benzenesulfonic acid monohydrate (169 g) was gradually added dropwise. After the reaction mixture was stirred at room temperature for 15 minutes, isopropyl ether (3670 mL) was added and stirred at room temperature for 2.5 hours. The precipitated crystal was collected by filtration to give the titled compound (345 g, white powder).

Workup

  1. stirringAfter the reaction mixture was stirred at room temperature for 15 minutes
  2. stirringstirred at room temperature for 2.5 hours
  3. filtrationThe precipitated crystal was collected by filtration

Sources & evidence

ORD record
ord-716aa939671c4ae2bc842b562bb714c9
Source dataset
uspto-grants-2007_10
Patent number
US07279584B2

Reaction notes

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