Ammonium Hydroxide → HCID 66658201, compound
Reaction equation
[OH-].[NH4+:2].[C:3]([C:10]1[S:14][C:13]([N+:15]([O-:17])=[O:16])=[C:12]([S:18](Cl)(=[O:20])=[O:19])[C:11]=1[CH2:22][NH:23][S:24]([CH3:27])(=[O:26])=[O:25])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]>C(#N)C>[C:3]([C:10]1[S:14][C:13]([N+:15]([O-:17])=[O:16])=[C:12]([S:18]([NH2:2])(=[O:20])=[O:19])[C:11]=1[CH2:22][NH:23][S:24]([CH3:27])(=[O:26])=[O:25])([O:5][C:6]([CH3:9])([CH3:8])[CH3:7])=[O:4]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Concentrated aqueous ammonium hydroxide solution (3 mL) was added to a solution of Boc-4-(methanesulfonylamino-methyl)-2-nitro-thiophene-3-sulfonyl chloride (3.30 g, 7.59 mmol) in acetonitrile (90 mL) at 0° C. The mixture was stirred at 0° C. for 45 min, and then was partitioned between half-saturated aqueous sodium bicarbonate solution (150 mL) and ethyl acetate (2×150 mL). The combined organic layers were dried over sodium sulfate, filtered and were concentrated in vacuo. Purification of the residue by flash column chromatography (Teledyne Isco RediSep column; 20-90% ethyl acetate in hexanes) afforded the desired product, Boc-4-(methanesulfonylamino-methyl)-2-nitro-thiophene-3-sulfonic acid amide (2.64 g, 6.35 mmol, 84%), as a yellow solid. 1H NMR (400 MHz, CDCl3) δ: 1.54 (9H, s), 3.35 (3H, s), 5.12 (2H, s), 5.81 (2H, bs), 7.61 (1H, s).
Workup
- customwas partitioned between half-saturated aqueous sodium bicarbonate solution (150 mL) and ethyl acetate (2×150 mL)
- dry with materialThe combined organic layers were dried over sodium sulfate
- filtrationfiltered
- concentrationwere concentrated in vacuo
- customPurification of the residue by flash column chromatography (Teledyne Isco RediSep column; 20-90% ethyl acetate in hexanes)
Sources & evidence
- ORD record
- ord-d7c27d16a3a64bb58bc6f8bd8e2618e5
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08097613B2
Reaction notes
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