4-Acetamidobenzenesulfonyl azide → 2-{2-Chloro-4-[2-(2-cyclopentyl-5-imino-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-phenyl}-2-methyl-propionitrile

HRID 1438306Notes

Reaction equation

HRID 1438306 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH2:15][C:14](=[O:16])[CH2:13][C:12](=[O:17])[O:11]2)[CH:5]=[CH:4][C:3]=1[C:23]([CH3:27])([CH3:26])[C:24]#[N:25].C([NH:31]C1C=CC(S(N=[N+]=[N-])(=O)=O)=CC=1)(=O)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][C:10]2([CH:18]3[CH2:19][CH2:20][CH2:21][CH2:22]3)[CH2:15][C:14](=[O:16])[C:13](=[NH:31])[C:12](=[O:17])[O:11]2)[CH:5]=[CH:4][C:3]=1[C:23]([CH3:27])([CH3:26])[C:24]#[N:25]

Participants

4

Reactant 2

HCID 51291854-Acetamidobenzenesulfonyl azideHCID 498714082-{2-Chloro-4-[2-(2-cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-phenyl}-2-methyl-propionitrile

Product 1

HCID 690546662-{2-Chloro-4-[2-(2-cyclopentyl-5-imino-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-phenyl}-2-methyl-propionitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred solution of 2-{2-chloro-4-[2-(2-cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-phenyl}-2-methyl-propionitrile (0.5 g, 1.29 mmol) from step 5 of example B(22), and p-acetamidobenzenesulfonyl azide (0.46 g, 1.94 mmol) in THF (4 mL) under argon was added TEA (0.54 mL, 3.87 mmol). The resulting solution was stirred at 25° C. overnight. The solvents were removed and the residue was purified by flash column chromatography (25-60% % EtOAc in hexanes) to give the product as a yellow oil. ESIMS (MH+): 414.

Workup

  1. customThe solvents were removed
  2. customthe residue was purified by flash column chromatography (25-60% % EtOAc in hexanes)

Sources & evidence

ORD record
ord-ee772d0b5e0e422a978834b0cbcfe800
Source dataset
uspto-grants-2009_11
Patent number
US07622605B2

Reaction notes

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