HCID 86636267, compound → tert-Butyl (3-{[(3-aminobenzyl)sulfonyl]amino}phenyl)carbamate

HRID 541826Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][CH:28]=1)[CH2:7][S:8]([NH:11][C:12]1[CH:13]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=[CH:16][CH:17]=1)(=[O:10])=[O:9])([O-])=O>O.CO.C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:26]=[CH:27][CH:28]=1)[CH2:7][S:8]([NH:11][C:12]1[CH:13]=[C:14]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH:15]=[CH:16][CH:17]=1)(=[O:10])=[O:9]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution tert-butyl (3-{[(3-nitrobenzyl)sulfonyl]amino}phenyl)carbamate (1.1 g, 2.7 mmol) in water (2 mL), methanol (100 mL) and acetic acid (4.1 mL) was added iron (0.60 g, 11.0 mmol) powder in one batch. The mixture was stirred at 0° C. for 2 h. The mixture was mixed with celite, filtered, and the cake was washed with EtOAc. The brown filtrate was concentrated and EtOAc and NaHCO3/water were added. The water layer was extracted with EtOAc once more. The organic layers were combined, dried over Na2SO4 and concentrated to give the desired product as a yellow powder (0.9 g, 90%). LCMS for C18H23N3O4S (M-tBu+H)+: m/z=322.0. 1H NMR (400 MHz, DMSO-d6): δ 9.72 (s, 1H), 9.39 (s, 1H), 7.44 (br, 1H), 7.16 (t, J=8.2 Hz, 1H), 7.12 (m, 1H), 6.94 (t, J=7.7 Hz, 1H), 7.79 (dt, J=7.2, 2.1 Hz, 1H), 6.50 (m, 1H), 6.49 (s, 1H), 6.35 (m, 1H).

Workup

additionThe mixture was mixed with celite
filtrationfiltered
washthe cake was washed with EtOAc
concentrationThe brown filtrate was concentrated
additionEtOAc and NaHCO3/water were added
extractionThe water layer was extracted with EtOAc once more
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-4551297eee1841c0af934854f5698d9a
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

Loading…