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

HRID 478026Notes

Reaction equation

HRID 478026 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-0698c519cccf486e829b6e97964ea67a
Source dataset
uspto-grants-1989_12
Patent number
US04889869

Reaction notes

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