Water → ethyl (2R)-2-(acetylamino)-3-(3-nitrophenyl)propanoate

HRID 47705

反応式

HRID 47705 の反応式
[C:1]([NH:4][CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].C(=O)([O-])O.[NH4+].O>C(#N)C>[C:1]([NH:4][C@H:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 962WaterHCID 14013Ammonium BicarbonateHCID 22292739Ethyl 2-(acetylamino)-3-(3-nitrophenyl)propanoate

生成物 1

HCID 86584419ethyl (2R)-2-(acetylamino)-3-(3-nitrophenyl)propanoate収率 50%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of 2.8 g of ethyl 2-(acetylamino)-3-(3-nitrophenyl)propanoate in 17 cm3 of acetonitrile [lacuna] to which is added 3.95 g of ammonium hydrogen carbonate and 35 cm3 of water at a pH in the region of 8. 0.017 g of type-II α-chymotrypsin is then introduced and the mixture is left stirring at room temperature for 1 hour 15 min, while measuring the pH regularly. After this reaction time, the pH is less than 8, a further 0.017 g of type-II α-chymotrypsin is added and stirring of the reaction medium is continued for 2 hours 45 min. The aqueous phase is extracted with 3 times 50 cm3 of ethyl acetate; the combined organic phases are then dried over sodium sulfate, filtered and evaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C. 1.4 g of ethyl (2R)-2-(acetylamino)-3-(3-nitrophenyl)propanoate are obtained in the form of white crystals melting at 110° C.

後処理

  1. addition0.017 g of type-II α-chymotrypsin is then introduced
  2. waitthe mixture is left
  3. additionAfter this reaction time, the pH is less than 8, a further 0.017 g of type-II α-chymotrypsin is added
  4. stirringstirring of the reaction medium
  5. waitis continued for 2 hours 45 min
  6. extractionThe aqueous phase is extracted with 3 times 50 cm3 of ethyl acetate
  7. dry with materialthe combined organic phases are then dried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated under reduced pressure (2 kPa) at a temperature in the region of 40° C

出典と根拠

ORDレコード
ord-ae19ad4a9f554c3ebcf9eb8e690ab98e
出典データセット
uspto-grants-2004_03
特許番号
US06699895B2

関連ノート

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