Trifluoroacetic acid → HCID 23598702, compound

HRID 891212Notes

Reaction equation

HRID 891212 reaction equation
C([O:3][CH:4]1[CH:8]([NH:9][C:10]([CH2:12][N:13]2[C:19](=[O:20])[CH:18]([NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:17][S:16](=[O:31])(=[O:30])[CH2:15][CH2:14]2)=[O:11])[CH2:7][C:6](=[O:32])[O:5]1)C.FC(F)(F)C(O)=O>C(#N)C.O>[OH:3][CH:4]1[CH:8]([NH:9][C:10]([CH2:12][N:13]2[C:19](=[O:20])[CH:18]([NH:21][C:22](=[O:29])[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:17][S:16](=[O:31])(=[O:30])[CH2:15][CH2:14]2)=[O:11])[CH2:7][C:6](=[O:32])[O:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23598700HCID 23598700, compound

Product 1

HCID 23598702HCID 23598702, compound

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

A solution of N-{4-[(2-ethoxy-5-oxo-tetrahydro-furan-3-ylcarbamoyl)-methyl]-1,1,5-trioxo-1λ6-[1,4]thiazepan-6-yl}-benzamide, 45, (0.03 g, 0.05 mmol) in acetonitrile/water is treated with trifluoroacetic acid. After stirring for 3 hours the solution is concentrated in vacuo and the crude product purified by preparative reverse phase HPLC to afford 0.02 g (77% -yield) of the desired product as a white solid.) 1H NMR (CD3OD): δ 7.90 (m, 2H), 7.62–7.46 (m, 3H), 5.46 (d, J=10.5 Hz, 1H), 4.61 (m, 1H), 4.51 (dd, J=16.3, 5.1 Hz, 1H), 4.36 (m, 2H), 4.02 (dd, J=16.0, 3.3 Hz, 1H), 3.84–3.64 (m, 3H), 3.42 (m, 1H), 3.26 (m, 1H), 2.68 (m, 1H), 2.52 (m, 1H); ESI MS 440.06 (M+H).

Workup

  1. concentrationis concentrated in vacuo
  2. customthe crude product purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-d9ef85d5f34b4d7eac462bb2c08952be
Source dataset
uspto-grants-2006_02
Patent number
US07001899B2

Reaction notes

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