Dicyclohexylcarbodiimide → 1-[3-(acetylthio)-2-methoxycarbonylmethylpropanoyl]-L-proline tert-butyl ester

HRID 1448007Notes

Reaction equation

HRID 1448007 reaction equation
[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][NH:8]1)([CH3:4])([CH3:3])[CH3:2].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[C:38]([S:41][CH2:42][CH:43]([CH2:47][C:48]([O:50][CH3:51])=[O:49])[C:44](O)=[O:45])(=[O:40])[CH3:39]>ClCCl>[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:44](=[O:45])[CH:43]([CH2:47][C:48]([O:50][CH3:51])=[O:49])[CH2:42][S:41][C:38](=[O:40])[CH3:39])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 127744283-Acetylthio-2-methoxycarbonylmethylpropanoic acid

Product 1

HCID 545040181-[3-(acetylthio)-2-methoxycarbonylmethylpropanoyl]-L-proline tert-butyl esterYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of L-proline tert-butyl ester (1.71 g) and 3-hydroxybenzotriazole (1.35 g) in dichloromethane (15 ml), dicyclohexylcarbodiimide (2.06 g) and 3-acetylthio-2-methoxycarbonylmethylpropanoic acid (2.2 g) are added. After eighteen hours stirring at room temperature, the precipitate formed is filtered off, the filtrate is washed neutral, dried, and concentrated to dryness to yield 3.7 g of 1-[3-(acetylthio)-2-methoxycarbonylmethylpropanoyl]-L-proline tert-butyl ester. Rf =0.8 (silica gel-ethyl acetate).

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off
  3. washthe filtrate is washed neutral
  4. customdried
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-0029b9412a3841769e0cbc85e2fd26d6
Source dataset
uspto-grants-1979_12
Patent number
US04179434

Reaction notes

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