N-Methylbutylamine → HCID 178449120、化合物

HRID 651983ノート

反応式

HRID 651983 の反応式
[N+:1]([N:4]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:5]([C:13]([OH:15])=O)[CH2:6][CH2:7][CH2:8][NH:9][C:10](=[NH:12])[NH2:11])([O-:3])=[O:2].ClC(OCC(C)C)=O.[CH3:31][NH:32][CH2:33][CH2:34][CH2:35][CH3:36]>O1CCCC1.C(N(CC)CC)C>[N+:1]([N:4]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:5]([C:13]([N:32]([CH2:33][CH2:34][CH2:35][CH3:36])[CH3:31])=[O:15])[CH2:6][CH2:7][CH2:8][NH:9][C:10](=[NH:12])[NH2:11])([O-:3])=[O:2]

参加物

6

反応物 3

HCID 8068N-MethylbutylamineHCID 62365Isobutyl chloroformateHCID 178454196HCID 178454196、化合物

生成物 1

HCID 178449120HCID 178449120、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

A 3.2 gram amount of NG -nitro-N2 -(tert-butyloxycarbonyl)-L-arginine was dissolved in a mixture of 40 ml of dry tetrahydrofuran and 1.4 ml of triethylamine. To the solution was added 1.4 ml of isobutyl chloroformate with stirring and cooling in an ice-salt bath. After additional stirring for 15 minutes, 0.87 gram of N-methyl-n-butylamine was added to the mixture. Then the reaction mixture was stirred continuously for 40 minutes at room temperature. The solvent was removed by distillation under reduced pressure, below 40° C. The residue was extracted with 100 ml of ethyl acetate and the extract was washed successively with a 10% aqueous citric acid solution, saturated sodium chloride solution, saturated aqueous sodium bicarbonate solution, and finally with saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated to give NG -nitro-N2 -(tert-butyloxy-carbonyl)-N-(n-butyl)-N-methyl-L-argininamide. This material was added to ethyl acetate containing 10% dry HCl and allowed to stand for 2 hours, and NG -nitro-N-(n-butyl)-N-methyl-L-argininamide hydrochloride was precipitated.

後処理

  1. temperaturecooling in an ice-salt bath
  2. stirringAfter additional stirring for 15 minutes
  3. stirringThen the reaction mixture was stirred continuously for 40 minutes at room temperature
  4. customThe solvent was removed by distillation under reduced pressure, below 40° C
  5. extractionThe residue was extracted with 100 ml of ethyl acetate
  6. washthe extract was washed successively with a 10% aqueous citric acid solution, saturated sodium chloride solution, saturated aqueous sodium bicarbonate solution
  7. dry with materialThe organic layer was dried over anhydrous Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-7f704b810709429686d61fd9d7b9079c
出典データセット
uspto-grants-1987_06
特許番号
US04670420

反応ノート

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