NBD-Cl → (S)-1-[2-Methyl-3-[(4-nitrobenzofurazan-7-yl)thio]-1-oxopropyl]-L-proline

HRID 1075304Notes

Reaction equation

HRID 1075304 reaction equation
[SH:1][CH2:2][CH:3]([CH3:14])[C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5].Cl[C:16]1[C:21]2=[N:22][O:23][N:24]=[C:20]2[C:19]([N+:25]([O-:27])=[O:26])=[CH:18][CH:17]=1.C(=O)(O)[O-].[Na+]>ClCCl>[CH3:14][CH:3]([CH2:2][S:1][C:16]1[C:21]2[C:20](=[N:24][O:23][N:22]=2)[C:19]([N+:25]([O-:27])=[O:26])=[CH:18][CH:17]=1)[C:4]([N:6]1[CH2:13][CH2:12][CH2:11][C@H:7]1[C:8]([OH:10])=[O:9])=[O:5]

Participants

5

Reactant 3

HCID 25043NBD-ClHCID 516892Sodium BicarbonateHCID 128775471-(2-Methyl-3-sulfanylpropanoyl)-L-proline

Product 1

HCID 22823694(S)-1-[2-Methyl-3-[(4-nitrobenzofurazan-7-yl)thio]-1-oxopropyl]-L-proline

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

700 Mg of 1-(3-mercapto-2-methyl-1-oxopropyl)-L-proline, 700 mg of 4-chloro-7-nitrobenzofurazan (10% excess), 1 g sodium bicarbonate, and 10 ml dichloromethane were stirred at 20° C. for 16 hours. The reaction mixture was put in a 4×30 cm Silicar CC4 column, and eluted with C6H6 :CH3COOH (3:1) mixture (v/v).

Workup

  1. washeluted with C6H6 :CH3COOH (3:1) mixture (v/v)

Sources & evidence

ORD record
ord-5d648ce7d2f54ef0be26b6ca10d3f356
Source dataset
uspto-grants-1983_07
Patent number
US04395556

Reaction notes

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