Triethylamine → Phenylmethyl[(4-fluoro-3-nitrophenyl)sulfonyl]methylcarbamate

HRID 536048Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](NC)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[CH2:16]([N:18](CC)CC)C.Cl[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>C1COCC1>[C:28]1([CH2:27][O:26][C:24](=[O:25])[NH:18][CH2:16][S:8]([C:5]2[CH:6]=[CH:7][C:2]([F:1])=[C:3]([N+:13]([O-:15])=[O:14])[CH:4]=2)(=[O:9])=[O:10])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4-fluoro-N-methyl-3-nitrobenzenesulfonamide (2 g, 8.54 mmol) in THF (20 mL) was treated with triethylamine (2.380 mL, 17.08 mmol) followed by dropwise addition of benzyl chloroformate (3.75 mL, 11.10 mmol). The mixture was stirred at 25° C. for 5 hours before being concentrated. The residue was treated with water and extracted with CH2Cl2. The organic extracts were washed (brine), dried (sodium sulfate), concentrated, and subjected to flash chromatography (25-50% EtOAc-hexanes) to give a yellow solid, which was suspended in EtOAc-hexanes, collected by filtration, and washed with hexanes to give phenylmethyl[(4-fluoro-3-nitrophenyl)sulfonyl]methylcarbamate (1 g, 32%) as a white solid. MS (m/z) 391.0 (M+Na+).

Workup

concentrationbefore being concentrated
additionThe residue was treated with water
extractionextracted with CH2Cl2
washThe organic extracts were washed (brine)
dry with materialdried (sodium sulfate)
concentrationconcentrated
customto give a yellow solid, which
filtrationcollected by filtration
washwashed with hexanes

Sources & evidence

ORD record: ord-5fbc59d946834d32b3392f206718bdd9
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08859571B2

Reaction notes

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