4-Chloro-3-nitro-1,2-dihydropyridin-2-one → tert-butyl{(2R)-1-hydroxy-3-[(3-nitro-2-oxo-1,2-dihydropyridin-4-yl)sulfanyl]propan-2-yl}carbamate

HRID 714139Notes

Reaction equation

HRID 714139 reaction equation
Cl[C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[N+:9]([O-:11])=[O:10].[C:12]([O:16][C:17](=[O:24])[NH:18][C@@H:19]([CH2:22][SH:23])[CH2:20][OH:21])([CH3:15])([CH3:14])[CH3:13]>CCO>[C:12]([O:16][C:17](=[O:24])[NH:18][C@@H:19]([CH2:22][S:23][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[C:3]=1[N+:9]([O-:11])=[O:10])[CH2:20][OH:21])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 5192824-Chloro-3-nitro-1,2-dihydropyridin-2-oneHCID 29925397Boc-Cysteinol

Product 1

HCID 88563545tert-butyl{(2R)-1-hydroxy-3-[(3-nitro-2-oxo-1,2-dihydropyridin-4-yl)sulfanyl]propan-2-yl}carbamateYield 69.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 4-chloro-3-nitropyridin-2(1H)-one (1.61 g, 9.2 mmol) (or any other suitable activated aromatic compound) and TEA (2 ml, 14.4 mmol) in etanol (15 mL) stirred at 0° C., was treated with a solution of tert-butyl[(2R)-1-hydroxy-3-sulfanylpropan-2-yl]carbamate (42, 2.073 g, 10 mmol) in ethanol (10 mL+5 ml rinse) added from syringe. The final mixture was stirred at room temperature for 22 h (became a thick yellow suspension). Filtered, the cake washed with pentane and dried under vacuum, to afford the title compound (2.20 g, 69% yield) as a yellow solid, MS: m/z=368.1 (MNa+).

Workup

  1. additionadded from syringe
  2. filtrationFiltered
  3. washthe cake washed with pentane
  4. customdried under vacuum

Sources & evidence

ORD record
ord-0e59a9fd5a49406ab97b90e6ff74fdc0
Source dataset
uspto-grants-2015_11
Patent number
US09187415B2

Reaction notes

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