Potassium Carbonate → N-[2-[[(1,1-dimethylethoxy)carbonyl]-amino]-4-(methylthio)-1-oxobutyl]-beta-alanine, ethyl ester

HRID 378128

Reaction equation

HRID 378128 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH2:11][S:12][CH3:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:18]([O:20][C:21](=[O:25])[CH2:22][CH2:23][NH2:24])[CH3:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.N1C=CC=CC=1.CN(C1C=CN=CC=1)C.C([O-])(O)=O.[Na+]>[CH3:4][C:1]([CH3:2])([O:5][C:6]([NH:8][CH:9]([CH2:10][CH2:11][S:12][CH3:13])[C:14]([NH:24][CH2:23][CH2:22][C:21]([O:20][CH2:18][CH3:19])=[O:25])=[O:16])=[O:7])[CH3:3]

Participants

8

Reactant 3

HCID 11430Potassium CarbonateHCID 89857Boc-L-methionineHCID 458475beta-Alanine, ethyl ester, hydrochloride

Product 1

HCID 85152754N-[2-[[(1,1-dimethylethoxy)carbonyl]-amino]-4-(methylthio)-1-oxobutyl]-beta-alanine, ethyl esterYield 81.2%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A solution of N-(tert-butoxycarbonyl)-L-methionine (6.2 g) in DMF (25 ml) and pyridine (25 ml) was treated with DSC (9.6 g) and a catalytic amount of DMAP. After 4 hours, a solution of β-alanine ethyl ester HCl (3.8 g) and K2CO3 (3.5 g) in saturated aqueous NaHCO3 (25 ml) was added. The reaction mixture was stirred overnight at room temperature. The excess solvent was removed under reduced pressure and purified by HPLC (RP--CH3CN/H2O). N-[2-[[(1,1-dimethylethoxy)carbonyl]-amino]-4-(methylthio)-1-oxobutyl]-β-alanine, ethyl ester (7.0 g) as a colorless oil was obtained. The oil was confirmed as the desired product by MS and used without further purification.

Workup

  1. customThe excess solvent was removed under reduced pressure
  2. custompurified by HPLC (RP--CH3CN/H2O)

Sources & evidence

ORD record
ord-432072e6407141fb8de154a6a1b3c967
Source dataset
uspto-grants-2000_02
Patent number
US06028223

Linked notes

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