Dichloromethane → HCID 178478819, compound

HRID 1984925Notes

Reaction equation

HRID 1984925 reaction equation
C(OC(=O)[NH:7][CH:8]([NH:17][CH2:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([CH2:25][NH:26][S:27]([C:30]2[CH:35]=[CH:34][C:33]([Br:36])=[CH:32][C:31]=2[O:37][C:38]([F:41])([F:40])[F:39])(=[O:29])=[O:28])[CH2:21][CH2:20]1)[NH:9]C(OC(C)(C)C)=O)(C)(C)C.C(Cl)[Cl:44]>C(O)(C(F)(F)F)=O>[ClH:44].[ClH:44].[Br:36][C:33]1[CH:34]=[CH:35][C:30]([S:27]([NH:26][CH2:25][C@H:22]2[CH2:23][CH2:24][C@H:19]([CH2:18][NH:17][C:8]([NH2:9])=[NH:7])[CH2:20][CH2:21]2)(=[O:29])=[O:28])=[C:31]([O:37][C:38]([F:40])([F:39])[F:41])[CH:32]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 178454269HCID 178454269, compound

Product 1

HCID 178478819HCID 178478819, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of trans-[({4-[(4-bromo-2-trifluoromethoxy-benzenesulfonylamino)-methyl]-cyclohexylmethyl}-amino)-tert-butoxycarbonylamino-methyl]-carbamic acid tert-butyl ester (53 mg, 0.077 mmol) in 50% TFA in CH2Cl2 (2 mL) was stirred at ambient temperature for 3 hr and the reaction mixture was concentrated. To the residue was added a solution of 1 M HCl in Et2O (0.5 mL) and the mixture was concentrated to give trans-4-Bromo-N-(4-guanidinomethyl-cyclohexylmethyl)-2-trifluoromethoxy-benzenesulfonamide dihydrochloride as a white solid (29 mg, 68%).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. additionTo the residue was added a solution of 1 M HCl in Et2O (0.5 mL)
  3. concentrationthe mixture was concentrated

Sources & evidence

ORD record
ord-f54be28f707b420c8c5fef98670b7adb
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

Loading…