Hydrochloric Acid → HCID 59168801, compound

HRID 1515965Notes

Reaction equation

HRID 1515965 reaction equation
Cl.C([C:9]1[S:13][C:12]([N+:14]([O-:16])=[O:15])=[C:11]([S:17]([NH2:20])(=[O:19])=[O:18])[C:10]=1[CH2:21][NH:22][S:23]([CH3:26])(=[O:25])=[O:24])(OC(C)(C)C)=O>O1CCOCC1>[CH3:26][S:23]([NH:22][CH2:21][C:10]1[C:11]([S:17]([NH2:20])(=[O:19])=[O:18])=[C:12]([N+:14]([O-:16])=[O:15])[S:13][CH:9]=1)(=[O:24])=[O:25]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66658201HCID 66658201, compound

Product 1

HCID 59168801HCID 59168801, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
25 °C

Procedure

Hydrogen chloride (20 mL of a 4.0 M solution in 1,4-dioxane) was added to a solution of Boc-4-(methanesulfonylamino-methyl)-2-nitro-thiophene-3-sulfonic acid amide (0.600 g, 1.44 mmol) in 1,4-dioxane (10 mL) at 25° C. The mixture was stirred at 25° C. for 18 h, 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; 60-100% ethyl acetate in hexanes) provided a yellow oil. This material was triturated with dichloromethane to afford a yellow solid that was collected by filtration to afford the desired product, 4-(methanesulfonylamino-methyl)-2-nitro-thiophene-3-sulfonic acid amide (0.400 g, 1.27 mmol, 88%). 1H NMR (400 MHz, DMSO-d6) δ: 2.96 (3H, s), 3.31 (2H, s), 4.35 (1H, d, J=5.4 Hz), 7.61 (1H, t, J=6.2 Hz), 7.85 (1H, s), 7.87 (2H, bs).

Workup

  1. customwas partitioned between half-saturated aqueous sodium bicarbonate solution (150 mL) and ethyl acetate (2×150 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationwere concentrated in vacuo
  5. customPurification of the residue by flash column chromatography (Teledyne Isco RediSep column; 60-100% ethyl acetate in hexanes)
  6. customprovided a yellow oil
  7. customThis material was triturated with dichloromethane
  8. customto afford a yellow solid
  9. filtrationthat was collected by filtration

Sources & evidence

ORD record
ord-55c3ca1585744f6b98c4f8eaf937197e
Source dataset
uspto-grants-2012_07
Patent number
US08222404B2

Reaction notes

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