Trifluoroacetic acid → HCID 86759201, compound

HRID 987221Notes

Reaction equation

HRID 987221 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].NCCCOC1C=CN2C(C=1)=CC(C(NC[C@H](NS(C1C=CC=CC=1)(=O)=O)C(O)=O)=O)=CC2=O.C([O:46][C:47](=[O:87])[C@@H:48]([NH:77][S:78]([C:81]1[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=1)(=[O:80])=[O:79])[CH2:49][NH:50][C:51]([C:53]1[CH:54]=[C:55]2[N:60]([C:61](=[O:63])[CH:62]=1)[CH:59]=[CH:58][C:57]([O:64][CH2:65][CH2:66][CH2:67][CH2:68][NH:69]C(OC(C)(C)C)=O)=[CH:56]2)=[O:52])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:69][CH2:68][CH2:67][CH2:66][CH2:65][O:64][C:57]1[CH:58]=[CH:59][N:60]2[C:55]([CH:56]=1)=[CH:54][C:53]([C:51]([NH:50][CH2:49][C@H:48]([NH:77][S:78]([C:81]1[CH:82]=[CH:83][CH:84]=[CH:85][CH:86]=1)(=[O:80])=[O:79])[C:47]([OH:87])=[O:46])=[O:52])=[CH:62][C:61]2=[O:63]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 56619444HCID 56619444, compoundHCID 86759202HCID 86759202, compound

Product 1

HCID 86759201HCID 86759201, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Using the procedure described for the preparation of compound XXX (step E), (S)-2-benzenesulfonylamino-3-{[8-(4-tert-butoxycarbonylamino-butoxy)-4-oxo-4H-quinolizine-2-carbonyl]-amino}-propionic acid tert-butyl ester (38 mg, 0.058 mmol) was treated with trifluoroacetic acid in dichloromethane to afford compound XXXII (32 mg, 90%) as a yellow solid which was characterized by 1HNMR (400 MHz, CD3OD) δ: 9.06 (1H, d, J=8.0 Hz), 7.86 (2H, dd, J=1.2, 7.7 Hz), 7.46-7.54 (3H, m), 7.23 (1H, d, J=2.5 Hz), 7.07 (1H, d, J=1.2 Hz), 7.03 (1H, dd, J=2.7, 8.0 Hz), 6.59 (1H, d, J=1.6 Hz), 4.27 (2H, t, J=5.7 Hz), 4.22 (1H, dd, J=5.1, 8.6 Hz), 3.79 (1H, dd, J=5.0, 13.4 Hz), 3.51 (1H, dd, J=8.6, 13.5 Hz), 3.06 (2H, t, J=7.4 Hz), 1.88-2.01 (4H, 2 multiplets).

Sources & evidence

ORD record
ord-4cb32d4ddfcb4fb786863b3f5bcb39f5
Source dataset
uspto-grants-2003_10
Patent number
US06630488B1

Reaction notes

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