4-Acetamidobenzenesulfonyl azide → HCID 58762625, compound

HRID 1453310Notes

Reaction equation

HRID 1453310 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]2([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[O:17][C:16](=[O:18])[CH2:15][C:14](=[O:19])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].P([O-])(O)(O)=O.[Na+].C(NC1C=CC(S([N:44]=[N+:45]=[N-])(=O)=O)=CC=1)(=O)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12]2([CH:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[O:17][C:16](=[O:18])[C:15](=[N+:44]=[N-:45])[C:14](=[O:19])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 51291854-Acetamidobenzenesulfonyl azideHCID 160761096-(3-chloro-4-methoxyphenethyl)-6-cyclopentyl-dihydro-3H-pyran-2,4-dioneHCID 23672064Monosodium phosphate

Product 1

HCID 58762625HCID 58762625, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-[2-(3-chloro-4-methoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione (0.500 g, 1.44 mmol) from Example B(87), and sodium dihydrogen phosphate (0.26 g, 2.16 mmol) in DMF (6 mL) was added 4-acetamidobenzenesulfonyl azide (0.52 g, 2.16 mmol). The reaction was stirred for 4 hours, and then concentrated by rotary evaporation. The crude material was purified by flash chromatography to yield the desired compound (0.537 g, 100% yield).

Workup

  1. concentrationconcentrated by rotary evaporation
  2. customThe crude material was purified by flash chromatography

Sources & evidence

ORD record
ord-afbe3a6e0b084e968ac36c20237f3b79
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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