HCID 57962595, compound → HCID 57962444, compound

HRID 541823Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([NH:13][C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O>O.CO.C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6]([S:10]([NH:13][C:14]2[CH:15]=[C:16]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:25])([CH3:24])[CH3:26])[CH:17]=[CH:18][CH:19]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution tert-butyl (3-{[(3-nitrophenyl)sulfonyl]amino}phenyl)carbamate (0.51 g, 0.0013 mol) in water (1 mL), methanol (5 mL) and acetic acid (2 mL) was added iron (290 mg, 5.2 mmol) powder in one batch. The mixture was stirred at 0° C. for 0.5 h. The reaction mixture was mixed with celite, filtered, and the cake was washed with EtOAc. The brown filtrate was concentrated, followed by the addition of EtOAc and NaHCO3/water. The aqueous phase was extracted with EtOAc. The organics were combined, dried over Na2SO4 and concentrated to give the desired product as a yellow powder (0.46 g, 98%). LCMS for C17H21N3O4S (M-tBu+H)+: m/z=308.0. 1H NMR (400 MHz, DMSO-d6): δ 10.02 (s, 1H), 9.31 (s, 1H), 7.33 (br, 1H), 7.10 (t, J=8.0 Hz, 1H), 7.02 (m, 1H), 6.93 (t, J=2.0 Hz, 1H), 6.85 (ddd, J=7.6, 1.8, 1.0 Hz, 1H), 6.67 (m, 1H), 5.53 (s, 1H), 1.43 (s, 9H).

Workup

additionThe reaction mixture was mixed with celite
filtrationfiltered
washthe cake was washed with EtOAc
concentrationThe brown filtrate was concentrated
additionfollowed by the addition of EtOAc and NaHCO3/water
extractionThe aqueous phase was extracted with EtOAc
dry with materialdried over Na2SO4
concentrationconcentrated

Sources & evidence

ORD record: ord-22a697af9d7a48688b82c924e954b8f2
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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