Acetonitrile → 1-[3-Acetylthio-3-(4-bromobenzoyl)propionyl]-L-proline methyl ester

HRID 903443Notes

Reaction equation

HRID 903443 reaction equation
[CH3:1][O:2][C:3](=[O:23])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:22])[CH2:10][CH:11]([C:13](=[O:21])[C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)Br.C(#N)C.[C:27]([O-:30])(=[S:29])[CH3:28].[K+]>CCOCC>[CH3:1][O:2][C:3](=[O:23])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9](=[O:22])[CH2:10][CH:11]([S:29][C:27](=[O:30])[CH3:28])[C:13](=[O:21])[C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 23670855Potassium ethanethioateHCID 541386821-[3-(4-Bromobenzoyl)-3-bromopropionyl]-L-proline methyl ester

Product 1

HCID 542165061-[3-Acetylthio-3-(4-bromobenzoyl)propionyl]-L-proline methyl ester

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of 5.28 g. of 1-[3-(4-bromobenzoyl)-3-bromopropionyl)-L-proline methyl ester (Example 30) in 35 ml. of acetonitrile is added 1.48 g. of potassium thioacetate. The mixture is stirred at room temperature for 2 hours, filtered and the filtrate is evaporated to dryness in vacuo leaving an amber gum. This is dissolved in ether and chromatographed on a 1"×16" silica gel column, eluting with ether and taking 100 ml. cuts. Cut number 3 gives the desired product (1.64 g.) as a glass.

Workup

  1. filtrationfiltered
  2. customthe filtrate is evaporated to dryness in vacuo
  3. customleaving an amber gum
  4. customchromatographed on a 1"×16" silica gel column
  5. washeluting with ether

Sources & evidence

ORD record
ord-b72709c3f8aa401591ce49aa194fa727
Source dataset
uspto-grants-1980_10
Patent number
US04226775

Reaction notes

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