Diisopropylethylamine → HCID 178454054, compound

HRID 1984942Notes

Reaction equation

HRID 1984942 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH2:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.[Br:25][C:26]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[C:28]([O:36][C:37]([F:40])([F:39])[F:38])[CH:27]=1>C(Cl)Cl>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([NH:14][S:32]([C:29]2[CH:30]=[CH:31][C:26]([Br:25])=[CH:27][C:28]=2[O:36][C:37]([F:40])([F:38])[F:39])(=[O:34])=[O:33])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27364214-Bromo-2-(Trifluoromethoxy)Benzene-1-Sulfonyl ChlorideHCID 178419079HCID 178419079, compound

Product 1

HCID 178454054HCID 178454054, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of trans-(4-amino-cyclohexyl)-carbamic acid tert-butyl ester (1 g, 0.0047 mol) in CH2Cl2 were added diisopropylethylamine (1.63 mL, 0.0093 mol) and 4-bromo-2-trifluoromethoxy-benzenesulfonyl chloride (1.03 mL, 0.0051 mol). The reaction mixture was stirred at ambient temperature for 1 hr and then washed with water. The aqueous layer was extracted with CH2Cl2 (twice), the organic layers were combined, dried over MgSO4, and concentrated. The resulting precipitate was recrystallized with CH2Cl2 and hexanes to give trans-[4-(4-bromo-2-trifluoromethoxy-benzenesulfonylamino)-cyclohexyl]-carbamic acid tert-butyl ester (2.39 g, 0.0046 mol, 99%).

Workup

  1. washwashed with water
  2. extractionThe aqueous layer was extracted with CH2Cl2 (twice), the organic layers
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe resulting precipitate was recrystallized with CH2Cl2 and hexanes

Sources & evidence

ORD record
ord-a87dc7edfe8e481bbf49d92595486934
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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