Triethylamine → ethyl N-carbethoxyvalerimidate

HRID 36174

反応式

HRID 36174 の反応式
[C:1](=[NH:9])([O:6][CH2:7][CH3:8])[CH2:2][CH2:3][CH2:4][CH3:5].C(N(CC)CC)C.Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C(Cl)Cl>[C:18]([N:9]=[C:1]([O:6][CH2:7][CH3:8])[CH2:2][CH2:3][CH2:4][CH3:5])([O:20][CH2:21][CH3:22])=[O:19]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 12283340Ethyl valerimidate

生成物 1

HCID 53930077ethyl N-carbethoxyvalerimidate収率 70%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 6.5 g (50.3 mmole) of ethyl valerimidate (free base) in 90 ml of dry CH2Cl2 was treated with 7.71 ml (5.60 g, 55.3 mole) of triethylamine. The resulting solution was stirred under N2 at -10° C. in an ice-salt bath as a solution of 4.81 ml (5.46 g, 50.3 mole) of ethyl chloroformate in 10 ml of CH2Cl2 was added dropwise over 25 minutes. Upon completion of the addition, the cooling bath was removed, and the mixture was stirred at room temperature for 2 hours. Next, the solvent was removed by evaporation in vacuo. The residue was taken up in hexane and filtered to remove triethylamine hydrochloride. Concentration of the filtrate yielded 7.08 g (70%) of the product as a yellow oil, suitable for use in the next step without further purification. NMR indicated a mixture of syn and anti isomers. TLC (98:2 CH2Cl2 --MeOH) showed a close pair of spots, Rf 0.48, 0.52; mass spectrum (EI) m/e 201 (M+).

後処理

  1. additionwas added dropwise over 25 minutes
  2. additionUpon completion of the addition
  3. customthe cooling bath was removed
  4. customNext, the solvent was removed by evaporation in vacuo
  5. filtrationfiltered
  6. customto remove triethylamine hydrochloride

出典と根拠

ORDレコード
ord-d5265fc594aa44e79a396715921d6262
出典データセット
uspto-grants-1995_05
特許番号
US05411980

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