Trifluoroacetic acid → 3-Benzyloxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid hydroxyamide

HRID 1872237Notes

Reaction equation

HRID 1872237 reaction equation
C([O:14][NH:15][C:16]([CH:18]1[CH:24]([CH2:25][O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH2:22][CH2:21][CH2:20][N:19]1[S:34]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)(=[O:36])=[O:35])=[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]([CH2:25][O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:23][CH2:22][CH2:21][CH2:20][N:19]1[S:34]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[CH:39][CH:38]=1)(=[O:36])=[O:35])=[O:17]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 544390273-Benzyloxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid benzhydryloxy-amide

Product 1

HCID 186896263-Benzyloxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid hydroxyamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-Benzyloxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid benzhydryloxy-amide (10 mg, 0.016 mmoL) in 0.25 mL of dichloromethane at 0° C. was added 0.25 mL of trifluoroacetic acid followed by triethyl silane (3.7 mg, 0.032 mmoL). After 50 minutes the solvent was removed under reduced pressure and the residue was azeotroped twice with toluene. The residue was then purified by column chromatography (silica: 1.5% to 3% methanol in dichloromethane) to yield 3-Benzyloxymethyl-1-(4-methoxy-benzenesulfonyl)-azepane-2-carboxylic acid hydroxyamide; MS: (M-H)- =447.

Workup

  1. customAfter 50 minutes the solvent was removed under reduced pressure
  2. customthe residue was azeotroped twice with toluene
  3. customThe residue was then purified by column chromatography (silica: 1.5% to 3% methanol in dichloromethane)

Sources & evidence

ORD record
ord-4d91785c74b2480faa45159451bfeee6
Source dataset
uspto-grants-2000_08
Patent number
US06107291

Reaction notes

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