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

HRID 478026노트

반응식

HRID 478026 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0698c519cccf486e829b6e97964ea67a
출처 데이터셋
uspto-grants-1989_12
특허 번호
US04889869

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