Trifluoroacetic acid → HCID 136381128, compound

HRID 53582Notes

Reaction equation

HRID 53582 reaction equation
C(OCC1CSC2N(C(=O)C2NC(=O)CC2N=C(C3C=CC=CC=3O)SC=2)C=1C(O)=O)(=O)C.C1(C([O:47][C:48]([C:50]2[N:51]3[CH:54]([S:55][CH2:56][CH:57]=2)[CH:53]([NH:58][C:59](=[O:74])[CH2:60][C:61]2[N:62]=[C:63]([C:66]4[C:71]([OH:72])=[CH:70][CH:69]=[CH:68][C:67]=4[OH:73])[S:64][CH:65]=2)[C:52]3=[O:75])=[O:49])C2C=CC=CC=2)C=CC=CC=1.[SiH](CC)(CC)CC.FC(F)(F)C(O)=O>C(Cl)CCl>[OH:72][C:71]1[CH:70]=[CH:69][CH:68]=[C:67]([OH:73])[C:66]=1[C:63]1[S:64][CH:65]=[C:61]([CH2:60][C:59]([NH:58][CH:53]2[C:52](=[O:75])[N:51]3[CH:54]2[S:55][CH2:56][CH:57]=[C:50]3[C:48]([OH:49])=[O:47])=[O:74])[N:62]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 136381123HCID 136381123, compoundHCID 136381129HCID 136381129, compound

Product 1

HCID 136381128HCID 136381128, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The procedure used for the preparation of 9a was repeated with 8g (145 mg, 0.242 mmol), Et3SiH (0.387 mL, 2.42 mmol), and trifluoroacetic acid (0.746 mL, 9.68 mmol) in dry ClCH2CH2Cl (6 mL) at 0° C. under nitrogen to give 9g (90.5 mg, 86%) as a white solid after crystallization from THF/CH2Cl2 /hexane. mp 165° C. (dec); IR (KBr) 3550-2550 (br), 3282, 1779, 1725, 1665, 1469, 1235 cm-1 ; 1H NMR (DMSO-d6) δ3.43-3.62 (2H, m), 3.76 (2H, s, CH2), 5.00 (1H, d, J=4.8 Hz), 5.67-5.73 (1H, m), 6.42 (3H, d, J=8.1 Hz), 7.07 (1H, t, J=8.1 Hz), 7.41 (1H, s), 9.11 (1H, d, J=8.2 Hz, NH), 12.17 (2H, br s, OH), 13.16 (1H, br s, CO2H); FDMS m/z 433 (M+), 434 (M+ +1); HRMS m/z Calcd for C18H16N3O6S2 (M+ +1): 434.0481, Found: 434.0448.

Sources & evidence

ORD record
ord-b47b0d6028b14c888e54f8ffae91f35b
Source dataset
uspto-grants-1997_04
Patent number
US05620968

Reaction notes

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