Trifluoroacetic acid → HCID 86590805, compound

HRID 722722Notes

Reaction equation

HRID 722722 reaction equation
C([O:3][CH:4]1[CH:8]([NH:9][C:10]([C@H:12]2[N:23]3[C@@H:16]([CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]([NH:25][C:26](=[O:33])[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:22]3=[O:24])[CH2:15][N:14]([S:34]([CH3:37])(=[O:36])=[O:35])[CH2:13]2)=[O:11])[CH2:7][C:6](=[O:38])[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]([C@H:12]2[N:23]3[C@@H:16]([CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]([NH:25][C:26](=[O:33])[C:27]4[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:22]3=[O:24])[CH2:15][N:14]([S:34]([CH3:37])(=[O:36])=[O:35])[CH2:13]2)=[O:11])[CH2:7][C:6](=[O:38])[O:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58741999HCID 58741999, compound

Product 1

HCID 86590805HCID 86590805, compound

Reagents, catalysts & solvents 1

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

Procedure

A solution of (4S,6S,10aS)-6-benzoylamino-2-methanesulfonyl-5-oxo-decahydro-2,4a-diaza-benzocyclooctene-4-carboxylic acid (2-ethoxy-5-oxo-tetrahydrofuran-3-yl)amide, 15, (70 mg, 0.13 mmol) in acetonitrile/water is treated with trifluoroacetic acid. After stirring for 30 minutes the solution is concentrated in vacuo and the crude product purified by preparative reverse phase HPLC to afford the desired product. 1H NMR (CD3OD) δ 7.90–7.88 (d, J=6.9 Hz, 2H), 7.52–7.55 (t, J=7.2 Hz, 1H), 7.52–7.47 (d, J=6.9 Hz, 2H), 5.14–5.11 (m, 2H), 4.69–4.67 (m, 1H), 4.54–4.49 (broad, d, J=12.6 Hz, 1H), 4.34–4.30 (m, 1H), 4.24–4.19 (broad d, J=12.9 HZ, 1H), 3.69–3.65 (d, J=12 Hz,1H), 3.40–3.28 (m, 3H), 3.09–3.04 (m,1H), 3.01 (s, 3H), 2.71–1.28 (m, 11H); MS 522.8 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-6c260218d8ef4cc2b29d1dc169b5b84e
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

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