Toluene → 2(S)-benzyloxycarbonylamino-3-cyclohexyl-propionic acid ethyl ester

HRID 478026ノート

反応式

HRID 478026 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[C:27]1(C)C=CC=C[CH:28]=1>C(O)C>[CH2:27]([O:14][C:13](=[O:15])[C@@H:12]([NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[CH3:28]

参加物

5

反応物 3

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 14158015(S)-2-(((Benzyloxy)carbonyl)amino)-3-cyclohexylpropanoic acid

生成物 1

HCID 141580172(S)-benzyloxycarbonylamino-3-cyclohexyl-propionic acid ethyl ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

243 g of 2(S)-benzyloxycarbonylamino-3-cyclohexylpropionic acid (manufacture: Helvetica Chimica Acta 57. 2131(1974)) are placed in 600 ml of toluene and 900 ml of ethanol. The reaction mixture is cooled to 0° and 88.3 g of thionyl chloride are added dropwise within 30 minutes. The cooling is removed and the mixture is stirred for 18 hours. The reaction mixture is filtered and the filtrate is concentrated. The residue is separated by means of flash chromatography (2 kg of silica gel 60, 40-63 μm, eluant F). The product-containing fractions are combined, concentrated by evaporation and dried under a high vacuum. The title compound is obtained in the form of a slightly yellowish oil. Rf (F)=0.2; Rf (B)=0.52.

後処理

  1. temperatureThe reaction mixture is cooled to 0°
  2. customThe cooling is removed
  3. filtrationThe reaction mixture is filtered
  4. concentrationthe filtrate is concentrated
  5. customThe residue is separated by means of flash chromatography (2 kg of silica gel 60, 40-63 μm, eluant F)
  6. concentrationconcentrated by evaporation
  7. customdried under a high vacuum

出典と根拠

ORDレコード
ord-0698c519cccf486e829b6e97964ea67a
出典データセット
uspto-grants-1989_12
特許番号
US04889869

反応ノート

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