2-Chloroethyldiisopropylammonium chloride → HCID 58875088, compound

HRID 2355254Notes

Reaction equation

HRID 2355254 reaction equation
CC(C)([O-])C.[K+].[C:7]1([S:13]([NH:16][C:17]2[CH:18]=[C:19]([C@@H:23]([OH:43])[CH2:24][NH:25][C:26]([CH3:42])([CH3:41])[CH2:27][CH2:28][N:29]3[C:37]4[C:32](=[CH:33][C:34]([C:38]([OH:40])=[O:39])=[CH:35][CH:36]=4)[CH:31]=[CH:30]3)[CH:20]=[CH:21][CH:22]=2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.[CH:45]([N:48]([CH:52]([CH3:54])[CH3:53])[CH2:49][CH2:50]Cl)([CH3:47])[CH3:46]>CN(C=O)C.C(OCC)(=O)C>[C:7]1([S:13]([NH:16][C:17]2[CH:18]=[C:19]([C@@H:23]([OH:43])[CH2:24][NH:25][C:26]([CH3:41])([CH3:42])[CH2:27][CH2:28][N:29]3[C:37]4[C:32](=[CH:33][C:34]([C:38]([O:40][CH2:50][CH2:49][N:48]([CH:52]([CH3:54])[CH3:53])[CH:45]([CH3:47])[CH3:46])=[O:39])=[CH:35][CH:36]=4)[CH:31]=[CH:30]3)[CH:20]=[CH:21][CH:22]=2)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 779422-Chloroethyldiisopropylammonium chlorideHCID 16660493HCID 16660493, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 58875088HCID 58875088, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium tert. butoxide (58 mg, 0.58 mmol) is added to a solution of 1-{3-[(R)-2-[3-(phenylsulphonylamino)-phenyl]-2-hydroxy-ethylamino]-3-methyl-butyl}-1H-indole-5-carboxylic acid [free base (Zwitterion) of Example 6; 300 mg, 0.58 mmol] in 2 ml DMF. Then the reaction mixture is stirred for 10 minutes at RT and 2-diisopropylamino-ethyl chloride hydrochloride (115 mg, 0.58 mmol) is added. After 72 hours stirring at RT the reaction mixture is diluted with 30 ml of ethyl acetate and extracted four times with 15 ml ice water. The organic phase is dried on magnesium sulphate, acidified with about 0.5 ml TFA and the solvent is eliminated in vacuo. The crude product is chromatographed on Microsorb C18-reverse-phase [acetonitrile (0.1% TFA)/water (0.13% TFA)=10:90→100:0].

Workup

  1. stirringAfter 72 hours stirring at RT the reaction mixture
  2. extractionextracted four times with 15 ml ice water
  3. customThe organic phase is dried on magnesium sulphate
  4. customThe crude product is chromatographed on Microsorb C18-reverse-phase [acetonitrile (0.1% TFA)/water (0.13% TFA)=10:90→100:0]

Sources & evidence

ORD record
ord-2e456cdf1ee24881884f9066e9e55065
Source dataset
uspto-grants-2010_07
Patent number
US07754756B2

Reaction notes

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