Ethanethiol → HCID 86612822, compound

HRID 1670018Notes

Reaction equation

HRID 1670018 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[CH3:16][CH2:17][SH:18].[C:19]([N:26]1[CH2:33][CH2:32][CH2:31][C@@H:27]1[C:28]([OH:30])=[O:29])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH2:17]([S:18][O:30][C:28](=[O:29])[C@H:27]1[CH2:31][CH2:32][CH2:33][N:26]1[C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH3:16]

Participants

6

Reactant 3

HCID 6343EthanethiolHCID 10868DicyclohexylcarbodiimideHCID 688022(2R)-1-[(tert-butoxy)carbonyl]pyrrolidine-2-carboxylic acid

Product 1

HCID 86612822HCID 86612822, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of DCC (2.55 g, 12.4 mmol), DMAP (100 mg), and EtSH (0.71 g, 11.1 mmol) in DCM was added dropwise a solution of (2R)-N-BOC-proline (3.00 g, 9.52 mmol) in DCM (30 mL). The reaction mixture was stirred at rt for 30 min, and filtered though Celite. The filtrate was dried over MgSO4 and concentrated in vacuo, and the residue was purified by column chomatography (EtOAc/Hex=1/4) to give the title compound (2.34 g, 95.2%).

Workup

  1. filtrationfiltered though Celite
  2. dry with materialThe filtrate was dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customthe residue was purified by column chomatography (EtOAc/Hex=1/4)

Sources & evidence

ORD record
ord-3cfe37494b9b4f0ab73e24c3c40a1420
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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