Hydrochloric Acid → ethyl (2R)-2-amino-3-cyclohexylpropanoate

HRID 47750

反応式

HRID 47750 の反応式
Cl.[CH:2]1([CH2:8][C@H:9]([C:11]([OH:13])=[O:12])[NH2:10])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.Cl.C(=O)([O-])[O-].[K+].[K+].[CH2:21](O)[CH3:22]>O>[NH2:10][C@H:9]([CH2:8][CH:2]1[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)[C:11]([O:13][CH2:21][CH3:22])=[O:12]

参加物

6

反応物 4

HCID 313Hydrochloric Acid2 回HCID 702Ethanol2 回HCID 11430Potassium CarbonateHCID 56777007(R)-2-Amino-3-cyclohexylpropanoic acid hydrochloride

生成物 1

HCID 86584436ethyl (2R)-2-amino-3-cyclohexylpropanoate

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

The process is performed as in Example 2, starting with 10 g of β-cyclohexyl-(D)-alanine hydrochloride in 96 cm3 of absolute ethanol, by treating it with a stream of dry hydrogen chloride at a temperature in the region of 0° C. for 20 minutes. After heating to about 80° C. for 4 days, followed by cooling to 0° C., the mixture is again treated with a stream of hydrogen chloride for 20 minutes, followed by heating to a temperature in the region of 80° C. for 20 hours. The reaction medium is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C., and the residue obtained is dissolved in 200 cm3 of water, made alkaline by addition of 19 g of solid potassium carbonate. After evaporation, the resulting solid is taken up in 200 cm3 of ethanol at a temperature in the region of 80° C. The insoluble material is filtered off and the filtrate is evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C. The residue obtained is taken up in 130 cm3 of ethanol at room temperature. The insoluble material is filtered off and the filtrate is again evaporated under the same conditions as above. 4.8 g of ethyl (2R)-2-amino-3-cyclohexylpropionate are obtained in the form of a whitish paste. (Rf=0.80 in a 90/10 by volume mixture of ethanol/aqueous ammonia, on a Merck 60F254R silica plate).

後処理

  1. temperatureby cooling to 0° C.
  2. temperatureby heating to a temperature in the region of 80° C. for 20 hours
  3. concentrationThe reaction medium is concentrated under reduced pressure (5 kPa) at a temperature in the region of 40° C.
  4. customthe residue obtained
  5. customAfter evaporation
  6. customis taken up in 200 cm3 of ethanol at a temperature in the region of 80° C
  7. filtrationThe insoluble material is filtered off
  8. customthe filtrate is evaporated under reduced pressure (5 kPa) at a temperature in the region of 40° C
  9. customThe residue obtained
  10. filtrationThe insoluble material is filtered off
  11. customthe filtrate is again evaporated under the same conditions as above

出典と根拠

ORDレコード
ord-d0bb066139384e1aabb91a939c97a086
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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