Sodium Bicarbonate → HCID 68820697, compound

HRID 736742Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

To a slurry of 2.0 g (13.77 mmol) of 4-amino-tetrahydro-furan-3-carboxylic acid methyl ester [WO 01/70673, Examples 46, 58] and 4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonyl chloride hydrochloride (5.13 g, 15.15 mmol) in CH2Cl2 (20 mL) was added saturated aqueous NaHCO3 (20 mL) at 0° C. The solution was allowed to warm to 25° C. over 19 h. The reaction was then diluted with CH2Cl2 (100 mL) and water (30 mL). The organic layer was washed with water (2×50 mL)and then dried over MgSO4, filtered and concentrated to obtain a crude oil (5.13 g ). The crude product was purified by Biotage Flash 40M chromatography, eluting with 1:1 ethyl acetate-hexanes, to afford 4-[4-(2-methyl-quinolin-4-ylmethoxy)-benzenesulfonylamino]-tetrahydro-furan-3-carboxylic acid methyl ester as a white solid (2.3 g, 38%). MS: 457 (M+H)+

Workup

washThe organic layer was washed with water (2×50 mL)
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customto obtain a crude oil (5.13 g )
customThe crude product was purified by Biotage Flash 40M chromatography
washeluting with 1:1 ethyl acetate-hexanes

Sources & evidence

ORD record: ord-32e9b1b3d1724bf4b0b52c8761f8eb84
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07595327B2

Reaction notes

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