Trifluoroacetic acid → HCID 136381132, compound

HRID 53584Notes

Reaction equation

HRID 53584 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][C:57]=2[Cl:58])[CH:53]([NH:59][C:60](=[O:74])[CH2:61][C:62]2[N:63]=[C:64]([C:67]4[C:72]([OH:73])=[CH:71][CH:70]=[CH:69][N:68]=4)[S:65][CH:66]=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>[Cl:58][C:57]1[CH2:56][S:55][CH:54]2[N:51]([C:52](=[O:75])[CH:53]2[NH:59][C:60](=[O:74])[CH2:61][C:62]2[N:63]=[C:64]([C:67]3[C:72]([OH:73])=[CH:71][CH:70]=[CH:69][N:68]=3)[S:65][CH:66]=2)[C:50]=1[C:48]([OH:49])=[O:47]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 136381123HCID 136381123, compoundHCID 136381133HCID 136381133, compound

Product 1

HCID 136381132HCID 136381132, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The procedure used for the preparation of 9a was repeated with 8j (186 mg, 0.301 mmol), Et3SiH (0.480 mL, 3.01 mmol), and trifluoroacetic acid (0.927 mL, 12.0 mmol) in dry ClCH2CH2Cl (6 mL) at 0° C. under nitrogen to give 9j (123 mg, 90%) a s a brownish solid after crystallization from THF/CH2Cl2 /hexane. mp 175° C. (dec); IR (KBr) 3600-2700 (br), 3277, 1780, 1730, 1663 cm-1 ; 1H NMR (DMSO-d6) δ3.63 (1H, d, J=18.0 Hz), 3.78 (2H, s, CH2), 3.98 (1H, d, J=18.0 Hz), 5.15 (1H, d, J=4.8 Hz), 5.69 (1H, dd, J=8.1 and 4.8 Hz), 7.37 (1H, dd, J=8.4 and 4.3 Hz), 7.44 (1H, dd, J=8.4 and 1.1 Hz), 7.58 (1H, s), 8.14 (1H, dd, J=4.3 and 1.1 Hz), 9.23 (1H, d, J=8.1 Hz, NH), 11.62 (1H, s, OH), 13.80 (1H, br s, CO2H); FDMS m/z 453 (M+ +1, 35Cl), 455 (M+ +1, 37Cl); HRMS m/z Calcd for C17H1435ClN4O5S2 (M+ +1): 453.0094, Found: 453.0090.

Sources & evidence

ORD record
ord-8bb5452f48b44fd48c5b7f710bbf8780
Source dataset
uspto-grants-1997_04
Patent number
US05620968

Reaction notes

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