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

HRID 378128

反応式

HRID 378128 の反応式
[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]

参加物

8

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒HCID 6228Dimethylformamide溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-432072e6407141fb8de154a6a1b3c967
出典データセット
uspto-grants-2000_02
特許番号
US06028223

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