(-)-Mandelic acid → (R)-2-Hydroxy-N-(4-nitrophenethyl)-2-phenylacetamide

HRID 76022ノート

反応式

HRID 76022 の反応式
Cl.[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][NH2:13])=[CH:7][CH:6]=1)([O-:4])=[O:3].[C:14](O)(=[O:23])[C@@H:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[OH:16].OC1C2N=NNC=2C=CC=1.Cl.CN(C)CCCN=C=NCC>O.Cl.CN(C)CCCN=C=NCC.CN(C)C=O.C(N(CC)CC)C>[OH:16][C@H:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:14]([NH:13][CH2:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:10][CH:9]=1)=[O:23]

参加物

9

反応物 4

HCID 11914(-)-Mandelic acidHCID 458983Benzeneethanamine, 4-nitro-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178418300HCID 178418300、化合物

生成物 1

HCID 59678380(R)-2-Hydroxy-N-(4-nitrophenethyl)-2-phenylacetamide収率 87.6%

試薬・触媒・溶媒 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

反応条件

温度
87 °C

実験手順

To a mixture of 5.90 kg of 4-nitrophenylethylamine monohydrochloride, 4.43 kg of (R)-mandelic acid, 2.94 kg of triethylamine and 22 liters of N,N-dimethylformamide were added 3.93 kg of hydroxybenztriazole and 5.58 kg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride (EDC) followed by stirring at about room temperature for 2 hours. EDC (0.28 kg) was further added thereto and the mixture was stirred at about room temperature throughout one night. The reaction solution was diluted with 110 liters of water and extracted with ethyl acetate (60 liters, 30 liters). The organic layer was successively washed with 60 liters of 1 M aqueous hydrochloric acid, 60 liters of 20% aqueous solution of potassium carbonate and water (60 liters, 60 liters) and concentrated in vacuo at 10 to 19° C. The residue was dissolved in 35 liters of toluene with heating at 87° C., cooled and stirred at 20° C. throughout one night. The resulting crystals were filtered and washed with 10 liters of toluene. This was dried in vacuo to give 7.66 kg of (R)-2-hydroxy-N-[2-(4-nitrophenyl)ethyl]-2-phenylacetamide as light yellow crystals.

後処理

  1. stirringthe mixture was stirred at about room temperature throughout one night
  2. extractionextracted with ethyl acetate (60 liters, 30 liters)
  3. washThe organic layer was successively washed with 60 liters of 1 M aqueous hydrochloric acid, 60 liters of 20% aqueous solution of potassium carbonate and water (60 liters, 60 liters)
  4. concentrationconcentrated in vacuo at 10 to 19° C
  5. dissolutionThe residue was dissolved in 35 liters of toluene
  6. temperaturecooled
  7. stirringstirred at 20° C. throughout one night
  8. filtrationThe resulting crystals were filtered
  9. washwashed with 10 liters of toluene
  10. customThis was dried in vacuo

出典と根拠

ORDレコード
ord-69cdc97cad39470e9e3502df895a0fae
出典データセット
uspto-grants-2014_09
特許番号
US08835474B2

反応ノート

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