Hydrochloric Acid → HCID 59168801, compound

HRID 2408798Notes

Reaction equation

HRID 2408798 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-b03c9bfd8f7543ea91515ea4e8758091
Source dataset
uspto-grants-2014_08
Patent number
US08815847B2

Reaction notes

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