Trifluoroacetic acid → HCID 86590804, compound

HRID 722721Notes

Reaction equation

HRID 722721 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]([C:34](=[O:36])[CH3:35])[CH2:13]2)=[O:11])[CH2:7][C:6](=[O:37])[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:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:22]3=[O:24])[CH2:15][N:14]([C:34](=[O:36])[CH3:35])[CH2:13]2)=[O:11])[CH2:7][C:6](=[O:37])[O:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 10459136HCID 10459136, compound

Product 1

HCID 86590804HCID 86590804, compound

Reagents, catalysts & solvents 1

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

Procedure

A solution of (4S,6S,10aS)-2-acetyl-6-benzoylamino-5-oxo-decahydro-2,4a-diaza-benzocyclooctene-4-carboxylic acid (2-ethoxy-5-oxo-tetrahydrofuran-3-yl)amide, 11, (70 mg, 0.14 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 36 mg of the desired product as a white solid. 1H NMR (CD3OD) δ 7.90 (d, J=6.9 Hz, 2H), 7.52 (m, 3H), 5.2–4.2 (series of m, 7H), 3.40 (m, 1H), 3.18 (m, 1H), 2.8–1.2 (series of m, 12H), 2.35 (s, 3H); MS 487 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-3ee7cece445840ca968e8ec1ade73885
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

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