Hydrochloric Acid → HCID 178514755, compound

HRID 2040150Notes

Reaction equation

HRID 2040150 reaction equation
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8]C(=O)OC(C)(C)C)[CH2:4][CH2:3]1.[H-].[Na+].F[C:19]1[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:21][C:20]=1[N+:29]([O-:31])=[O:30].Cl>O1CCCC1.O.ClCCl>[NH2:8][C@H:5]1[CH2:4][CH2:3][C@H:2]([O:1][C:19]2[CH:24]=[CH:23][C:22]([S:25]([NH2:28])(=[O:27])=[O:26])=[CH:21][C:20]=2[N+:29]([O-:31])=[O:30])[CH2:7][CH2:6]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 1514287cis-4-(tert-Butoxycarbonylamino)cyclohexanolHCID 167824874-Fluoro-3-nitrobenzenesulfonamide

Product 1

HCID 178514755HCID 178514755, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of tert-butyl 4-hydroxycyclohexylcarbamate (0.250 g) in tetrahydrofuran (5 mL) was added sodium hydride (0.186 g). After stirring for 15 minutes, 4-fluoro-3-nitrobenzenesulfonamide (0.256 g) was added as a solution in tetrahydrofuran (1 mL). The reaction was heated to 60° C. for 1.5 hours, cooled, and poured into a mixture of dichloromethane (100 mL) and water (25 ml). The aqueous layer was adjusted to pH˜4 with 1N aqueous HCl and the organic layer was separated, washed with brine (50 ml), dried over magnesium sulfate, filtered, and concentrated. The residue was loaded onto silica gel (GraceResolv 40 g) and eluted using a gradient of 0.5% to 7.5% methanol/dichloromethane over 30 minutes. This solid was treated with HCl (4.0M in dioxane, 5 ml) at room temperature for 1 hour and concentrated to give the title compound.

Workup

  1. temperaturecooled
  2. customthe organic layer was separated
  3. washwashed with brine (50 ml)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washeluted
  8. customover 30 minutes
  9. additionThis solid was treated with HCl (4.0M in dioxane, 5 ml) at room temperature for 1 hour
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-67647f6463f94d70abd010ffacc90563
Source dataset
uspto-grants-2013_11
Patent number
US08580794B2

Reaction notes

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