Sodium hydride → 3-[(6-Acetyl-2-chloro-pyridin-3-ylmethyl)-amino]-propionic acid tert-butyl ester

HRID 547274Notes

Reaction equation

HRID 547274 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:17]=[CH:18][C:19]([C:23](=[O:25])[CH3:24])=[N:20][C:21]=1[Cl:22]>CN(C=O)C>[C:2]([O:6][C:7](=[O:11])[CH2:8][CH2:9][NH:10][CH2:15][C:16]1[C:21]([Cl:22])=[N:20][C:19]([C:23](=[O:25])[CH3:24])=[CH:18][CH:17]=1)([CH3:5])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 16218890Tert-butyl 3-aminopropanoate hydrochlorideHCID 86011816Ethanone, 1-[5-(bromomethyl)-6-chloro-2-pyridinyl]-

Product 1

HCID 865959983-[(6-Acetyl-2-chloro-pyridin-3-ylmethyl)-amino]-propionic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 3-amino-propionic acid tert-butyl ester hydrochloride (1.5 eq) in DMF is added NaH (3.5 eq). The resulting mixture is stirred at room temperature for 15 minutes and a solution of 1-(5-bromomethyl-6-chloro-pyridin-2-yl)-ethanone (1 eq) in DMF is then added. After stirring for 3 hours, it is partitioned with 20% EtOAc/hexane and H2O. The organic layer is washed with brine and dried. After concentration, 3-[(6-acetyl-2-chloro-pyridin-3-ylmethyl)-amino]-propionic acid tert-butyl ester is isolated by flash column chromatography. MS: (ES+): 313.1 (M+1)+.

Workup

  1. stirringAfter stirring for 3 hours
  2. customit is partitioned with 20% EtOAc/hexane and H2O
  3. washThe organic layer is washed with brine
  4. customdried
  5. concentrationAfter concentration

Sources & evidence

ORD record
ord-8792f304bc2f4e5180e35d4541450ba2
Source dataset
uspto-grants-2011_05
Patent number
US07939519B2

Reaction notes

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