Hydrochloric Acid → HCID 178463346, compound

HRID 1944708Notes

Reaction equation

HRID 1944708 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]([O:20]C)=[O:19])[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[NH:22][CH2:23][CH3:24].Cl>C1COCC1.CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@H:12]2[CH2:13][CH2:14][C@H:15]([C:18]([OH:20])=[O:19])[CH2:16][CH2:17]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[NH:22][CH2:23][CH3:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178463347HCID 178463347, compound2×

Product 1

HCID 178463346HCID 178463346, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

Methyl trans-4-(4-chloro-3-(ethylamino)phenylsulfonamido)cyclohexane-carboxylate (Intermediate 12, 220 mg, 0.552 mmol) in 1/1/1 THF/MeOH/1N LiOH was warmed to 45° C. overnight. The reaction was cooled to room temperature, then acidified to pH 3 with 1N HCl and extracted with multiple volumes EtOAc. The combined organic layers were dried over sodium sulfate, filtered and concentrated to give the title compound as colorless solid (169 mg, 0.468 mmol, 85% yield). MS MH+ 361.2

Workup

  1. extractionextracted with multiple volumes EtOAc
  2. dry with materialThe combined organic layers were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-f655119199ca4ff0bcaf7a806b1bb25b
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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