Trifluoroacetic acid → HCID 136381130, compound

HRID 53583Notes

Reaction equation

HRID 53583 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[CH3:58])[CH:53]([NH:59][C:60](=[O:75])[CH2:61][C:62]2[N:63]=[C:64]([C:67]4[C:72]([OH:73])=[CH:71][CH:70]=[CH:69][C:68]=4[OH:74])[S:65][CH:66]=2)[C:52]3=[O:76])=[O:49])C2C=CC=CC=2)C=CC=CC=1.[SiH](CC)(CC)CC.FC(F)(F)C(O)=O>C(Cl)CCl>[OH:73][C:72]1[CH:71]=[CH:70][CH:69]=[C:68]([OH:74])[C:67]=1[C:64]1[S:65][CH:66]=[C:62]([CH2:61][C:60]([NH:59][CH:53]2[C:52](=[O:76])[N:51]3[CH:54]2[S:55][CH2:56][C:57]([CH3:58])=[C:50]3[C:48]([OH:49])=[O:47])=[O:75])[N:63]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 136381123HCID 136381123, compoundHCID 136381131HCID 136381131, compound

Product 1

HCID 136381130HCID 136381130, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The procedure used for the preparation of 9a was repeated with 8h (169 mg, 0.276 mmol), Et3SiH (0.441 mL, 2.76 mmol), and trifluoroacetic acid (0.849 mL, 11.0 mmol) in dry ClCH2CH2Cl (6 mL) at 0° C. under nitrogen to give 9h (121 mg, 98%) as a white solid after crystallization from THF/hexane. mp 155° C. (dec); IR (KBr) 3500-2500 (br), 1768, 1670, 1467 cm-1 ; 1H NMR (DMSO-d6) δ1.97 (3H, s, CH3), 3.31 (1H, d, J=18.0 Hz), 3.51 (1H, d, J=18.0 Hz), 3.76 (2H, s, CH2), 5.00 (1H, d, J=4.5 Hz), 5.57 (1H, dd, J=8.0 and 4.5 Hz), 6.42 (2H, d, J=8.1 Hz), 7.07 (1H, t, J=8.1 Hz), 7.41 (1H, s), 9.07 (1H, d, J=8.0 Hz, NH), 12.20 (2H, br s, OH), 13.20 (1H, br s, CO2H); FDMS m/z 448 (M+ +1); HRMS m/z Calcd for C19H18N3O6S2 (M+ +1): 448.0637, Found: 448.0607.

Sources & evidence

ORD record
ord-16b73a3ed91049e1a8cc7bc925ae9ac4
Source dataset
uspto-grants-1997_04
Patent number
US05620968

Reaction notes

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