Tris(2-carboxyethyl)phosphine → N-[2-(6-Amino-pyridine-2-carbonyl)-5-chloro-pyridin-3-yl]-4-tert-butyl-N-methoxymethyl-benzenesulfonamide

HRID 1898223Notes

Reaction equation

[N:1]([C:4]1[N:9]=[C:8]([C:10]([C:12]2[C:17]([N:18]([CH2:32][O:33][CH3:34])[S:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([CH3:31])([CH3:30])[CH3:29])=[CH:24][CH:23]=3)(=[O:21])=[O:20])=[CH:16][C:15]([Cl:35])=[CH:14][N:13]=2)=[O:11])[CH:7]=[CH:6][CH:5]=1)=[N+]=[N-].C(CCP(CCC(O)=O)CCC(O)=O)(O)=O>C1COCC1>[NH2:1][C:4]1[N:9]=[C:8]([C:10]([C:12]2[C:17]([N:18]([CH2:32][O:33][CH3:34])[S:19]([C:22]3[CH:27]=[CH:26][C:25]([C:28]([CH3:30])([CH3:31])[CH3:29])=[CH:24][CH:23]=3)(=[O:20])=[O:21])=[CH:16][C:15]([Cl:35])=[CH:14][N:13]=2)=[O:11])[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of N-[2-(6-azido-pyridine-2-carbonyl)-5-chloro-pyridin-3-yl]-4-tert-butyl-N-methoxymethyl-benzenesulfonamide (0.3 mmol, 155 mg) in THF (3 mL) was added 3-[bis-(2-carboxy-ethyl)-phosphanyl]-propionic acid (1 mmol, 250 mg). The mixture was stirred at 50° C. for 3 h. Upon completion of the reduction, the THF was removed under reduced pressure. The residue was diluted with EtOAc and the organics were washed with saturated sodium bicarbonate, dried with sodium sulfate, concentrated in vacuo, and purified via automated silica gel chromatography to generate the desired product. MS m/z: 489.1 (M+H)+.

Workup

customUpon completion of the reduction, the THF was removed under reduced pressure
additionThe residue was diluted with EtOAc
washthe organics were washed with saturated sodium bicarbonate
dry with materialdried with sodium sulfate
concentrationconcentrated in vacuo
custompurified

Sources & evidence

ORD record: ord-5341e89eabd84cc29a3823f8df7336c7
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08519135B2

Reaction notes

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