Dicyclohexylcarbodiimide → HCID 54504018, compound

HRID 263349Notes

Reaction equation

HRID 263349 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 54504018HCID 54504018, compoundYield 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-d5385dd4709c489596fb4c5875d48a8f
Source dataset
uspto-grants-1979_05
Patent number
US04156786

Reaction notes

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