Hydrochloric Acid → HCID 68536101, compound

HRID 1992835Notes

Reaction equation

HRID 1992835 reaction equation
[OH-].[Na+].[F:3][C:4]([F:43])([F:42])[S:5]([N:8]([C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:33][CH3:34])=[CH:30][CH:31]=3)[CH:26]=[C:25]([CH3:35])[C:24]=2[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:18][CH:17]=1)S(C(F)(F)F)(=O)=O)(=[O:7])=[O:6].Cl>C(Cl)Cl>[F:42][C:4]([F:3])([F:43])[S:5]([NH:8][C:16]1[CH:21]=[CH:20][C:19]([O:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:33][CH3:34])=[CH:30][CH:31]=3)[CH:26]=[C:25]([CH3:35])[C:24]=2[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)=[CH:18][CH:17]=1)(=[O:6])=[O:7]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86616642HCID 86616642, compound

Product 1

HCID 68536101HCID 68536101, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1 N Sodium Hydroxide (2 mL) was added to a solution of 30 (94 mg, 0.15 mmol, 1 equiv) in CH2Cl2 (2 mL) and the reaction mixture was stirred at RT for 3 days. The reaction was then acidified to pH 2 with 1 N HCl and the product extracted into CH2Cl2 (100 mL). The organic layer was washed with saturated aqueous NaHCO3 (2×50 mL), dried over MgSO4, filtered and concentrated to dryness. The residue was purified by silica gel flash column chomatography (20% EtOAc in hexanes) to provide 31 (47 mg, 64%) as a yellow oil. 1HNMR (400 MHz, DMSO-d6): δ 11.52 (br s, 1H), 7.69 (m, 1H), 7.57 (m, 1H), 7.34-7.21 (m, 4H), 7.15 (m, 2H), 7.07 (m, 1H), 6.99 (m, 2H), 6.59 (m, 2H), 3.86 (s, 3H), 2.16 (s, 3H). MS m/z 486.1 (M−H)−.

Workup

  1. extractionthe product extracted into CH2Cl2 (100 mL)
  2. washThe organic layer was washed with saturated aqueous NaHCO3 (2×50 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by silica gel flash column chomatography (20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-9e095cac99a74230b4243ccb0f003ce3
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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