Dicyclohexylcarbodiimide → N-Ethyl-n-heptyl-4-(4-(methylsulfonamido)phenyl)-4-oxobutanamide

HRID 466348

反応式

HRID 466348 の反応式
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:18])[CH2:13][CH2:14][C:15]([OH:17])=O)=[CH:8][CH:7]=1)(=[O:4])=[O:3].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[CH2:44]([NH:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[CH3:45]>CN(C=O)C>[CH2:44]([N:46]([CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH3:53])[C:15](=[O:17])[CH2:14][CH2:13][C:12](=[O:18])[C:9]1[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:11][CH:10]=1)[CH3:45]

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 480381-Heptanamine, N-ethyl-HCID 757711-HydroxybenzotriazoleHCID 113692744-(4-(Methylsulfonamido)phenyl)-4-oxobutanoic acid

生成物 1

HCID 14891420N-Ethyl-n-heptyl-4-(4-(methylsulfonamido)phenyl)-4-oxobutanamide

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
5 °C

実験手順

A stirred solution of 4-[(methylsulfonyl)amino]-γ-oxobenzenebutanoic acid as prepared in Preparation 2 (12.0 g, 0.044 mol) in DMF (100 ml) under N2 is cooled in an ice bath to 5° C. and treated with 1-hydroxybenzotriazole (5.94 g, 0.044 mol) and N,N'-dicyclohexylcarbodiimide (9.08 g, 0.044 mol). After 1 hour, ethylheptylamine (6.3 g, 0.044 mol) is added; after an additional 30 minutes the ice bath is removed and the mixture is kept at ambient temperature for 18 hours. The reaction mixture is filtered over a Celite filter aid and the filtrate is concentrated under vacuum. The resulting material is dissolved in CH2Cl2 ; washed with dilute HCl, NaHCO3 and brine; dried (Na2SO4) and concentrated. The residue is chromatographed over silica gel (1.25 kg) with 5% MeOH:1% NH4OH:CH2Cl2. The N-ethyl-N-heptyl-γ-oxo-4-[(methylsulfonyl)amino]benzenebutanamide thus obtained is crystallized from EtOAc:SSB to yield 10.77 g, mp 100°-102° C. and 2.32 g, mp 99°-101° C. The analytical sample has a mp 102°-103° C.

後処理

  1. customafter an additional 30 minutes the ice bath is removed
  2. waitthe mixture is kept at ambient temperature for 18 hours
  3. filtrationThe reaction mixture is filtered over a Celite
  4. filtrationfilter aid
  5. concentrationthe filtrate is concentrated under vacuum
  6. dissolutionThe resulting material is dissolved in CH2Cl2
  7. washwashed with dilute HCl, NaHCO3 and brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe residue is chromatographed over silica gel (1.25 kg) with 5% MeOH

出典と根拠

ORDレコード
ord-442fb2c8391a494ca284b2a676fcafd9
出典データセット
uspto-grants-1992_10
特許番号
US05155268

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