Dicyclohexylcarbodiimide → HCID 54504018, compound

HRID 569883Notes

Reaction equation

HRID 569883 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, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of L-proline t-butyl ester (1.71 g.) and 3-hydroxybenzotriazole (1.35 g.) in dichloromethane (15 ml.) dicyclohexylcarbodiimide (2.06 g.) and the product from Example 79 (2.2 g.) are added. After 18 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 the named product 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
  6. customto yield 3.7 g

Sources & evidence

ORD record
ord-66134870d5b945b59b6b9faba16cb4ff
Source dataset
uspto-grants-1988_03
Patent number
US04734420

Reaction notes

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