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

HRID 76022노트

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HRID 76022 반응식
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]

참가 물질

9

반응물 4

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

생성물 1

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

시약·촉매·용매 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride촉매HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매

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온도
87 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-69cdc97cad39470e9e3502df895a0fae
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835474B2

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