Dicyclohexylcarbodiimide → HCID 13192709, compound

HRID 1733349Notes

Reaction equation

HRID 1733349 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([CH2:7][S:8][CH2:9][CH:10]([C:14]([F:17])([F:16])[F:15])[C:11]([OH:13])=O)=[CH:5][CH:4]=1.[C:20]([O:24][C:25](=[O:31])[C@@H:26]1[CH2:30][CH2:29][CH2:28][NH:27]1)([CH3:23])([CH3:22])[CH3:21].C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:20]([O:24][C:25](=[O:31])[C@@H:26]1[CH2:30][CH2:29][CH2:28][N:27]1[C:11](=[O:13])[CH:10]([C:14]([F:17])([F:16])[F:15])[CH2:9][S:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:19][CH:18]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 12805629HCID 12805629, compound

Product 1

HCID 13192709HCID 13192709, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(4-methoxybenzyl)thio-2-trifluoromethylpropanoic acid (6.5 g.) and proline tert-butyl ester (3.76 g.) in dichloromethane (500 ml.) is stirred at 0° and treated with dicyclohexylcarbodiimide (4.53 g.) After 30 minutes at 0° and overnight at room temperature, the mixture is filtered and the filtrate is washed neutral. The organic layer is dried and concentrated to dryness in vacuo. The TLC [silica gel methylene chloride/ethyl acetate (95:5)] shows two major spots Rf 0.46 and 0.51 corresponding to the two diastereoisomers.

Workup

  1. filtrationthe mixture is filtered
  2. washthe filtrate is washed neutral
  3. customThe organic layer is dried
  4. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-53ea55ec621b499cbf469bf36e5f9b0f
Source dataset
uspto-grants-1980_12
Patent number
US04241076

Reaction notes

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