Triethylamine → (+/-)-2-[(Acetylthio)methyl]-4-methyl-N-[2-(1-piperidinyl)ethyl]pentanamide

HRID 444194ノート

反応式

HRID 444194 の反応式
[C:1]([S:4][CH2:5][CH:6]([CH2:10][CH:11]([CH3:13])[CH3:12])[C:7]([OH:9])=O)(=[O:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[NH2:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1>C1COCC1>[C:1]([S:4][CH2:5][CH:6]([CH2:10][CH:11]([CH3:13])[CH3:12])[C:7]([NH:27][CH2:28][CH2:29][N:30]1[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1)=[O:9])(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 33944N-(2-Aminoethyl)piperidineHCID 130175572-[(Acetylthio)methyl]-4-methylpentanoic acid

生成物 1

HCID 13017560(+/-)-2-[(Acetylthio)methyl]-4-methyl-N-[2-(1-piperidinyl)ethyl]pentanamide

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒4 回

反応条件

温度
-5 °C

実験手順

A solution of (±)-2-[(acetylthio)methyl]-4-methylpentanoic acid in 40 ml of THF is cooled to 5° C., followed by the dropwise addition of triethylamine (1.0 g) in 5 ml of THF. This solution is cooled to -5° C. and ethyl chloroformate in 4 ml of THF is added dropwise at -5° to 0° C. It is stirred for 30 minutes and N-(2-aminoethyl)piperidine in 30 ml of THF is added dropwise. The reaction mixture is stirred at 20° C. for 4 hours and stored at 0° C. for about 16 hours. Triethylamine hydrochloride is filtered off and the filtrate is concentrated in vacuo. The residue is dissolved in ether and washed with aqueous NaHCO3. Ether is dried with MgSO4, filtered and concentrated in vacuo to yield 2.1 g of crude product. This crude is absorbed on a 20-g pad of alumina act II and washed through with ether to yield 1.4 g of product which crystallizes from pentane, melting point 47°-50° C.

後処理

  1. stirringThe reaction mixture is stirred at 20° C. for 4 hours
  2. waitstored at 0° C. for about 16 hours
  3. filtrationTriethylamine hydrochloride is filtered off
  4. concentrationthe filtrate is concentrated in vacuo
  5. dissolutionThe residue is dissolved in ether
  6. washwashed with aqueous NaHCO3
  7. dry with materialEther is dried with MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto yield 2.1 g of crude product
  11. customThis crude is absorbed on a 20-g pad of alumina act II
  12. washwashed through with ether

出典と根拠

ORDレコード
ord-c459f6f524b44b9497a322d4f31028e8
出典データセット
uspto-grants-1981_04
特許番号
US04263293

反応ノート

読み込み中…