Dicyclohexylcarbodiimide → N-(3-Mercapto-2-methylpropanoyl)-L-Proline tert-butyl Ester

HRID 1252802Notes

Reaction equation

HRID 1252802 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].C1(N=C=NC2CCCCC2)CCCCC1.C([S:31][CH2:32][CH:33]([CH3:37])[C:34](O)=[O:35])(=O)C>ClCCl>[C:1]([O:5][C:6](=[O:12])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:34](=[O:35])[CH:33]([CH3:37])[CH2:32][SH:31])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1180733-(Acetylthio)-2-methylpropanoic acidHCID 6453108L-Proline 1,1-dimethylethyl ester

Product 1

HCID 54491354N-(3-Mercapto-2-methylpropanoyl)-L-Proline tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

L-Proline tert-butyl ester (5.1 g) is dissolved in dichloromethane (40 ml) and the solution stirred and chilled in an ice bath. Dicyclohexylcarbodiimide (6.2 g) dissolved in dichloromethane (15 ml) is added followed immediately by a solution of 3-acetylthio-2-methylpropanoic acid (4.9 g) in dichloromethane (5 ml). After 15 minutes stirring in the ice bath and 16 hours at room temperature, the precipitate is filtered off and the filtrate is concentrated to dryness in vacuo. The residue is dissolved in ethyl acetate and washed neutral. The organic phase is dried over magnesium sulfate and concentrated to dryness in vacuo. The residue, N-(3-acetylthio-2-methylpropanoyl)-L-proline tert-butyl ester, is purified by column chromatography (silica gel, chloroform), yield 7.9 g. The named product is obtained by following the procedure of Example 29, step (b).

Workup

  1. temperaturechilled in an ice bath
  2. additionis added
  3. filtrationthe precipitate is filtered off
  4. concentrationthe filtrate is concentrated to dryness in vacuo
  5. dissolutionThe residue is dissolved in ethyl acetate
  6. washwashed neutral
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. concentrationconcentrated to dryness in vacuo
  9. customThe residue, N-(3-acetylthio-2-methylpropanoyl)-L-proline tert-butyl ester, is purified by column chromatography (silica gel, chloroform), yield 7.9 g
  10. customThe named product is obtained

Sources & evidence

ORD record
ord-52f76e1f3aab432f856a1f41c913dd29
Source dataset
uspto-grants-1988_05
Patent number
US04745124

Reaction notes

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