Trifluoroacetic acid → 7-[[[2-(2-Hydroxyphenyl)-4-thiazolyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

HRID 53580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 53580
C(OC[C:6]1[CH2:13][S:12][CH:11]2[N:8]([C:9](=[O:30])[CH:10]2[NH:14][C:15](=[O:29])[CH2:16][C:17]2[N:18]=[C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[OH:28])[S:20][CH:21]=2)[C:7]=1[C:31]([OH:33])=[O:32])(=O)C.C1(C(OC(C2N3C(SCC=2)C(NC(=O)CC2N=C(C4C=CC=CC=4O)SC=2)C3=O)=O)C2C=CC=CC=2)C=CC=CC=1.[SiH](CC)(CC)CC.FC(F)(F)C(O)=O>C(Cl)CCl>[OH:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:19]1[S:20][CH:21]=[C:17]([CH2:16][C:15]([NH:14][CH:10]2[C:9](=[O:30])[N:8]3[CH:11]2[S:12][CH2:13][CH:6]=[C:7]3[C:31]([OH:33])=[O:32])=[O:29])[N:18]=1

Komponenten

6

Edukt 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 136381123HCID 136381123, VerbindungHCID 136381125HCID 136381125, Verbindung

Produkt 1

HCID 1363811247-[[[2-(2-Hydroxyphenyl)-4-thiazolyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic AcidAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

The procedure used for the preparation of 9a was repeated with 8c (184 mg, 0.316 mmol), Et3SiH (0.505 mL, 3.16 mmol), and trifluoroacetic acid (0.972 mL, 12.6 mmol) in dry ClCH2CH2Cl (4 mL) at 0° C. under nitrogen to give 9c (132 mg, 100%) as a white solid after crystallization from THF/Et2O/hexane. mp 185° C. (dec); IR (KBr) 3700-2800 (br), 3291, 1768, 1710, 1659, 1230 cm-1 ; 1H NMR (DMSO-d6) δ3.48 (1H, dd, J=19.0 and 6.0 Hz), 3.59 (1H, dd, J=19.0 and 2.6 Hz), 3.75 (2H, s, CH2), 5.01 (1H, d, J=4.9 Hz), 5.72 (1H, dd, J=8.2 and 4.9 Hz), 6.45 (1H, dd, J=6.0 and 2.6 Hz), 6.88 (1H, t, J=7.8 Hz), 6.96 (1H, d, J=7.8 Hz), 7.25 (1H, t, J=7.8 Hz), 7.41 (1H, s), 7.94 (1H, d, J=7.8 Hz), 9.08 (1H, d, J=8.2 Hz, NH), 11.30 (1H, s, OH), 13.14 (1H, br s, CO2H); FDMS m/z 417 (M+), 418 (M+ +1); Anal. Calcd for C18H15N3O5S2. (C4H8O) 0.20: C, 52.28; H, 3.87; N, 9.73. Found: C, 52.41; H, 3.62; N, 9.71

Quellen und Nachweise

ORD-Eintrag
ord-b3fe743a7d15460f928ec03d6c5623d1
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620968

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