Trifluoroacetic acid → HCID 86590808, compound

HRID 722734Notes

Reaction equation

HRID 722734 reaction equation
C([O:3][CH:4]1[CH:8]([NH:9][C:10]([C@H:12]2[N:17]3[C:18](=[O:33])[C@@H:19]([NH:24][C:25](=[O:32])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[CH2:20][CH:21]=[CH:22][CH2:23][C@@H:16]3[CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:7][C:6](=[O:34])[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:17]3[C:18](=[O:33])[C@@H:19]([NH:24][C:25](=[O:32])[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:20][CH:21]=[CH:22][CH2:23][C@H:16]3[CH2:15][CH2:14][CH2:13]2)=[O:11])[CH2:7][C:6](=[O:34])[O:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86590809HCID 86590809, compound

Product 1

HCID 86590808HCID 86590808, compound

Reagents, catalysts & solvents 1

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

Procedure

A solution of (4S,7S,11aS)-7-benzoylamino-6-oxo-1,3,4,6,7,8,11,11a-octahydro-2H-pyrido[1,2-a]azocine-4-carboxylic acid (2-ethoxy-5-oxo-tetrahydro-furan-3-yl)-amide, 45, (32 mg) in 10 mL of 1:1 acetonitrile/water is treated with 2 mL of 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 21 mg of the desired product as a white solid. 1H NMR (CD3OD) δ 7.92 (d, J=7.0 Hz, 2H), 7.54 (m, 3H), 5.75 (m, 1H), 5.63 (m, 1H), 5.42 (dd, J=8.1, 4.8 Hz, 1H), 5.01 (d, J=6.2 Hz, 1H), 4.72 (m, 1H0, 4.65 (d, J=4.0 Hz, 0.5H), 4.64 (d, J=4.0 Hz, 0.5 H), 4.31 (m, 1H), 3.18 (m, 1H), 2.68 (m, 2H), 2.45 (m, 3H), 2.26 (br d, J=13.9 Hz, 1H), 2.10 (m, 1H), 1.94 (m, 1H), 1.80 (br d, J=13.2 Hz, 1H), 1.61 (m, 2H); MS 442 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-4fac55acd56349bc84296935136a684b
Source dataset
uspto-grants-2006_11
Patent number
US07138395B2

Reaction notes

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