Sodium hydride → HCID 68452001, compound

HRID 2353368Notes

Reaction equation

HRID 2353368 reaction equation
Cl.[C:2]([O:6][C:7](=[O:11])[CH2:8][CH2:9][NH2:10])([CH3:5])([CH3:4])[CH3:3].[H-].[Na+].Br[CH2:15][C:16]1[CH:40]=[CH:39][C:19]2[N:20]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[C:25]([C:35]([F:38])([F:37])[F:36])[CH:24]=3)[S:22][C:18]=2[CH:17]=1>CN(C=O)C.CCOC(C)=O>[C:2]([O:6][C:7](=[O:11])[CH2:8][CH2:9][NH:10][CH2:15][C:16]1[CH:40]=[CH:39][C:19]2[N:20]=[C:21]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)=[C:25]([C:35]([F:36])([F:37])[F:38])[CH:24]=3)[S:22][C:18]=2[CH:17]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 16218890Tert-butyl 3-aminopropanoate hydrochlorideHCID 68451721HCID 68451721, compound

Product 1

HCID 68452001HCID 68452001, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of β-alanine tert-butyl ester hydrochloride (47 mg, 1.1 eq.) in DMF (2 ml) is added NaH (60% in mineral oil) (28 mg, 3 eq.) at room temperature. The mixture is stirred at room temperature for 15 minutes before a solution of 6-bromomethyl-2-(2-trifluoromethyl-biphenyl-4-yl)benzothiazole (105 mg, 0.234 mmol) in DMF (1 ml) is added. The mixture is stirred at room temperature overnight, diluted with EtOAc, washed with 10% Na2S2O3, brine, dried over MgSO4, filtered and concentrated. Column chromatography (CH2Cl2/CH3OH, 95/5) gave 31 mg (26%) of 3-{[2-(2-trifluoromethyl-biphenyl-4-yl)-benzothiazol-6-ylmethyl]-amino}-propionic acid tert-butyl ester.

Workup

  1. additionis added
  2. washwashed with 10% Na2S2O3, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-4cdf6486b8d847e6b16aaf417bc995cf
Source dataset
uspto-grants-2010_07
Patent number
US07750021B2

Reaction notes

Loading…