3-(Trifluoromethyl)benzoic acid → HCID 86594363, compound

HRID 351376Notes

Reaction equation

HRID 351376 reaction equation
[NH2:1][C@H:2]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]([C@H:9]2[CH2:14][CH2:13][C@@H:12]([N:15]=[N+:16]=[N-:17])[CH2:11][C@H:10]2[CH2:18][S:19]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)(=[O:21])=[O:20])[C:3]1=[O:28].[F:29][C:30]([F:41])([F:40])[C:31]1[CH:32]=[C:33]([CH:37]=[CH:38][CH:39]=1)[C:34](O)=[O:35].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[N:15]([C@@H:12]1[CH2:13][CH2:14][C@H:9]([N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C@H:2]([NH:1][C:34](=[O:35])[C:33]3[CH:37]=[CH:38][CH:39]=[C:31]([C:30]([F:29])([F:40])[F:41])[CH:32]=3)[C:3]2=[O:28])[C@H:10]([CH2:18][S:19]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)(=[O:20])=[O:21])[CH2:11]1)=[N+:16]=[N-:17]

Participants

7

Reactant 4

HCID 99633-(Trifluoromethyl)benzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21088239HCID 21088239, compound

Product 1

HCID 86594363HCID 86594363, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-amino-(3S)-1-(1S,2R,4R)-(4-azido-2-benzenesulfonylmethyl-cyclohexyl)-azepan-2-one (50 mg, 0.12 mmol) in DMF (15 mL) was added 3-trifluoromethyl benzoic acid (28 mg, 0.15 mmol), HATU (57 mg, 0.15 mmol) and Hunig's base (0.03 mL, 0.15 mmol). The resulting mixture was stirred for 16 h before EtOAc was added. The EtOAc layer was washed with 1 N HCl, NaHCO3 solution (aq), and brine. The EtOAc was dried (MgSO4), filtered, and concentrated. Flash chromatography of the resulting residue gave N-[(3S)-1-(1S,2R,4R)-(4-azido-2-benzenesulfonylmethyl-cyclohexyl)-2-oxo-azepan-3-yl]-3-trifluoromethyl-benzamide (70 mg). MS found: (M+H)+=578.

Workup

  1. additionwas added
  2. washThe EtOAc layer was washed with 1 N HCl, NaHCO3 solution (aq), and brine
  3. dry with materialThe EtOAc was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cd4d099226fb45cc80e126c9b233cc3f
Source dataset
uspto-grants-2007_02
Patent number
US07183270B2

Reaction notes

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