Trifluoroacetic acid → HCID 18689623, compound

HRID 1872268Notes

Reaction equation

HRID 1872268 reaction equation
C([O:14][NH:15][C:16]([CH:18]1[CH:24]([CH:25]([OH:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:23][CH:22]=[CH:21][CH2:20][N:19]1[S:33]([C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)(=[O:35])=[O:34])=[O:17])(C1C=CC=CC=1)C1C=CC=CC=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>ClCCl>[OH:14][NH:15][C:16]([CH:18]1[CH:24]([CH:25]([OH:32])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:23][CH:22]=[CH:21][CH2:20][N:19]1[S:33]([C:36]1[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=1)(=[O:35])=[O:34])=[O:17]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 54573955HCID 54573955, compound

Product 1

HCID 18689623HCID 18689623, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
12.5 °C

Procedure

A solution of 3-(hydroxy-phenyl-methyl)-1-(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid benzhydryloxy-amide (5 mg, 0.008 mmoL) in dichloromethane (1 mL) was cooled to 0° C. This solution was treated with trifluoroacetic acid (0.1 mL) followed by a 0.31 M solution of triethylsilane in dichloromethane (0.026 mL). The reaction mixture was warmed from 0 to 25° C. over 35 minutes and then the solvents were removed in vacuo and the residue was coevaporated with toluene. The residue was purified by flash chromatography (silica, 5 to 10% methanol in dichloromethane) to give 3-(hydroxy-phenyl-methyl)-1(4-methoxy-benzenesulfonyl)-2,3,4,7-tetrahydro-1H-azepine-2-carboxylic acid hydroxyamide as a white solid; MS: (M-H)- 430.9.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe residue was purified by flash chromatography (silica, 5 to 10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-514aecdcffaf478288c0c2424632ace0
Source dataset
uspto-grants-2000_08
Patent number
US06107291

Reaction notes

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