Dicyclohexylcarbodiimide → HCID 54491354, compound

HRID 262584Notes

Reaction equation

HRID 262584 reaction equation
[SH:1][CH2:2][CH:3]([CH3:7])[C:4](O)=[O:5].[C:8]([O:12][C:13](=[O:19])[C@@H:14]1[CH2:18][CH2:17][CH2:16][NH:15]1)([CH3:11])([CH3:10])[CH3:9].C1(N=C=NC2CCCCC2)CCCCC1>C(O)(=O)C.ClCCl>[C:8]([O:12][C:13](=[O:19])[C@@H:14]1[CH2:18][CH2:17][CH2:16][N:15]1[C:4](=[O:5])[CH:3]([CH3:7])[CH2:2][SH:1])([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 1529103-Mercaptoisobutyric acidHCID 6453108L-Proline 1,1-dimethylethyl ester

Product 1

HCID 54491354HCID 54491354, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To the cold (5°) solution of 1.2 g. (10 mMol.) of 3-mercapto-2-methylpropanoic acid and 1.7 g. (10 mMol.) of L-proline tert.butyl ester in 25 ml. dichloromethane 2.26 g. of dicyclohexylcarbodiimide in 5 ml. dichloromethane is added in portions. After 2 hours at room temperature, 5 drops of acetic acid are added, the mixture is filtered and the filtrate evaporated to an oily residue. This residue is taken up in 20 ml. of petroleum ether-ethyl acetate (3:1) and applied to a 150 ml. silica gel column prepared in petroleum ether. The fraction eluted with petroleum ether-ethyl acetate (1:1) contains the product, 1-(3-Mercapto-2-methylpropanoyl)-L-proline tert.butyl ester. This fraction (0.6 g.) is dried over P2O5 in vacuo for 12 hours. Rf 0.6 (Silica gel, Benzene/Acetic acid 3:1), Rf 0.8 (Silica gel, Methyl-ethylketone/acetic acid/pyridine/water 14:1:2:1).

Workup

  1. customTo the cold (5°) solution of 1.2 g
  2. filtrationthe mixture is filtered
  3. customthe filtrate evaporated to an oily residue
  4. customsilica gel column prepared in petroleum ether
  5. washThe fraction eluted with petroleum ether-ethyl acetate (1:1)
  6. dry with materialThis fraction (0.6 g.) is dried over P2O5 in vacuo for 12 hours

Sources & evidence

ORD record
ord-412ef96bc5c84fff8502d8ad785805e5
Source dataset
uspto-grants-1979_05
Patent number
US04154840

Reaction notes

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