(4-Nitrophenyl)acetic acid → di t-butyl 4-nitrobenzylcarbonyl-L-glutamate

HRID 619412

反応式

HRID 619412 の反応式
[OH:1][N:2]1C2C=CC=CC=2N=N1.[N+]([C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=O)=[CH:16][CH:15]=1)([O-])=O.[C:24]([O:28][C:29](=[O:41])[C@H:30]([CH2:32][CH2:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[NH2:31])([CH3:27])([CH3:26])[CH3:25].C1(N=C=NC2CCCCC2)CCCCC1.CN(C)C=[O:60]>>[N+:2]([CH:33]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:32][C@@H:30]([C:29]([O:28][C:24]([CH3:26])([CH3:27])[CH3:25])=[O:41])[NH:31][C:21]([CH2:20][C:17]1[CH:16]=[CH:15][CH:14]=[CH:19][CH:18]=1)=[O:23])([O-:1])=[O:60]

参加物

6

反応物 5

HCID 4661(4-Nitrophenyl)acetic acidHCID 6228DimethylformamideHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 208637L-Glutamic acid di-tert-butyl ester

生成物 1

HCID 86748613di t-butyl 4-nitrobenzylcarbonyl-L-glutamate収率 77%

実験手順

1-Hydroxybenzotriazole (4.05 g) was added to a solution of 4-nitrophenyl acetic acid (5.4 g) in dimethylformamide (75 ml). L-Glutamic acid di tert-butyl ester (7.77 g) and then dicyclohexylcarbodiimide (6.2 g) were added to the mixture. The mixture was then stirred for 18 hr at ambient temperature. The mixture was filtered and the filtrate washed with saturated sodium bicarbonate solution, water and 0.5 m hydrochloric acid and then dried and evaporated to dryness. The residue was chromatographed on silica gel by eluting with hexane/ethyl acetate (2:1) to give di t-butyl 4-nitrobenzylcarbonyl-L-glutamate as an oil 9.7 g (77%). NMR: 8.2(d)2H; 7.45(d)2H; 6.45(d)1H; 4.45(m)1H; 3.15(s)2H; 2.1(m)4H; 1.4(d)9H; 1.35(s)9H.

後処理

  1. filtrationThe mixture was filtered
  2. washthe filtrate washed with saturated sodium bicarbonate solution, water and 0.5 m hydrochloric acid
  3. customdried
  4. customevaporated to dryness
  5. customThe residue was chromatographed on silica gel
  6. washby eluting with hexane/ethyl acetate (2:1)

出典と根拠

ORDレコード
ord-fd6a939a4e6146c6a9f212db56b50549
出典データセット
uspto-grants-1999_09
特許番号
US05958971

関連ノート

読み込み中…