Trifluoroacetic acid → HCID 136381126, compound

HRID 53581Notes

Reaction equation

HRID 53581 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[CH2:58][O:59][C:60](=[O:62])[CH3:61])[CH:53]([NH:63][C:64](=[O:79])[CH2:65][C:66]2[N:67]=[C:68]([C:71]4[C:76]([OH:77])=[CH:75][CH:74]=[CH:73][C:72]=4[OH:78])[S:69][CH:70]=2)[C:52]3=[O:80])=[O:49])C2C=CC=CC=2)C=CC=CC=1.[SiH](CC)(CC)CC.FC(F)(F)C(O)=O>C(Cl)CCl>[C:60]([O:59][CH2:58][C:57]1[CH2:56][S:55][CH:54]2[N:51]([C:52](=[O:80])[CH:53]2[NH:63][C:64](=[O:79])[CH2:65][C:66]2[N:67]=[C:68]([C:71]3[C:76]([OH:77])=[CH:75][CH:74]=[CH:73][C:72]=3[OH:78])[S:69][CH:70]=2)[C:50]=1[C:48]([OH:49])=[O:47])(=[O:62])[CH3:61]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 136381123HCID 136381123, compoundHCID 136381127HCID 136381127, compound

Product 1

HCID 136381126HCID 136381126, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The procedure used for the preparation of 9a was repeated with 8e (181 mg, 0.270 mmol), Et3SiH (0.431 mL, 2.70 mmol), and trifluoroacetic acid (0.832 mL, 10.8 mmol) in dry ClCH2CH2Cl (6 mL) at 0° C. under nitrogen to give 9e (120 mg, 88%) as a white solid after crystallization from EtOAc/CH2Cl2 /hexane. mp 145° C. (dec); IR (KBr) 3650-2500 (br), 1775, 1736, 1466, 1237 cm-1 ; 1H NMR (DMSO-d6) δ1.98 (3H, s, CH3), 3.43 (1H, d, J=18.1 Hz ), 3.58 (1H, d, J=18.1 Hz), 3.76 (2H, s, CH2), 4.64 (1H, d, J=12.8 Hz), 4.95 (1H, d, J=12.8 Hz), 5.05 (1H, d, J=5.0 Hz), 5.64-5.70 (1H, m), 6.42 (2H, d, J=8.0 Hz), 7.07 (1H, t, J=8.0 Hz), 7.41 (1H, s), 9.12 (1H, d, J=8.1 Hz, NH), 12.17 (2H, br s, OH), 13.60 (1H, br s, CO2H); FDMS m/z 505 (M+), 506 (M+ +1); Anal. Calcd for C21H19N3O8S2 : C, 49.89; H, 3.79; N 8.31. Found. C 50.15; H 3.79; N 8.60.

Sources & evidence

ORD record
ord-1e7443bcd03e450a892e83141de1c3f7
Source dataset
uspto-grants-1997_04
Patent number
US05620968

Reaction notes

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