Trifluoroacetic acid → HCID 136381136, compound

HRID 53586Notes

Reaction equation

HRID 53586 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: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>[OH:73][C:72]1[C:67]([C:64]2[S:65][CH:66]=[C:62]([CH2:61][C:60]([NH:59][CH:53]3[C:52](=[O:75])[N:51]4[CH:54]3[S:55][CH2:56][C:57]([CH3:58])=[C:50]4[C:48]([OH:49])=[O:47])=[O:74])[N:63]=2)=[N:68][CH:69]=[CH:70][CH:71]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 136381123HCID 136381123, compoundHCID 136381137HCID 136381137, compound

Product 1

HCID 136381136HCID 136381136, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The procedure used for the preparation of 9a was repeated with 8l (167 mg, 0.279 mmol), Et3SiH (0.446 mL, 2.79 mmol), and trifluoroacetic acid (0.860 mL, 11.2 mmol) in dry ClCH2CH2Cl (6 mL) am 0° C. under nitrogen to give 9l (112 mg, 93%) as a yellowish solid after crystallization from THF/CH2Cl2 /hexane. mp 180° C. (dec); IR (KBr) 3540-2540 (br), 3280, 1774, 1725, 1661 cm-1 ; 1H NMR (DMSO-d6) δ1.97 (3H, s, CH3),3.30 (1H, d, J=18.0Hz), 3.51 (1H, d J=18.0 Hz), 3.79 (2H, s, CH2), 4.99 (1H, d, J=4.6 Hz), 5.56 (1H, dd, J=8.1 and 4.6 Hz), 7.37 (1H, dd, J=8.4 and 4.3 Hz), 7.44 (1H, dd, J=8.4 and 1.0 Hz), 7.58 (1H, s), 8.14 (1H, dd, J=4.3 and 1.0 Hz), 9.11 (1H, d, J=8.1 Hz, NH), 11.64 (1H, s, OH), 13.12 (1H, br s, CO2H); FDMS m/z 432 (M+), 433 (M+ +1); Anal. Calcd for C18H16N4O5S2 : C, 49.99; H, 3.73; N, 12.95. Found: C, 50.24; H, 3.58; N, 12.68.

Workup

  1. customam 0° C. under nitrogen

Sources & evidence

ORD record
ord-3ab2cd16915f47d1816e2bbb2758473f
Source dataset
uspto-grants-1997_04
Patent number
US05620968

Reaction notes

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