Trifluoroacetic acid → 7-[[[2-(3-Hydroxyphenyl)-4-thiazolyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid

HRID 53588Notes

Reaction equation

HRID 53588 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][CH:57]=2)[CH:53]([NH:58][C:59](=[O:73])[CH2:60][C:61]2[N:62]=[C:63]([C:66]4[CH:71]=[CH:70][CH:69]=[C:68]([OH:72])[CH:67]=4)[S:64][CH:65]=2)[C:52]3=[O:74])=[O:49])C2C=CC=CC=2)C=CC=CC=1.[SiH](CC)(CC)CC.FC(F)(F)C(O)=O>C(Cl)CCl>[OH:72][C:68]1[CH:67]=[C:66]([C:63]2[S:64][CH:65]=[C:61]([CH2:60][C:59]([NH:58][CH:53]3[C:52](=[O:74])[N:51]4[CH:54]3[S:55][CH2:56][CH:57]=[C:50]4[C:48]([OH:49])=[O:47])=[O:73])[N:62]=2)[CH:71]=[CH:70][CH:69]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 731922347-[[[2-(3-Hydroxyphenyl)-4-thiazolyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic Acid Diphenylmethyl EsterHCID 136381123HCID 136381123, compound

Product 1

HCID 731922377-[[[2-(3-Hydroxyphenyl)-4-thiazolyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic AcidYield 99.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The procedure used for the preparation of 9a was repeated with 8n (152 mg, 0.261 mmol), Et3SiH (0.417 mL, 2.61 mmol), and trifluoroacetic acid (0.804 mL, 10.4 mmol) in dry ClCH2CH2Cl (4 mL) at 0° C. under nitrogen to give 9n (108 mg, 99%) as a white solid after crystallization from THF/Et2O/hexane. mp 195° C. (dec); IR (KBr) 3600-2600 (br), 3343, 1787, 1682, 1532 cm-1 ; 1H NMR (DMSO-d6) δ3.49 (1H, dd, J=19.0 and 6.0 Hz), 3.59 (1H, dd, J=19.0 and 2.6 Hz ), 3.73 (2H, s, CH2), 5.01 (1H, d, J=4.9 Hz), 5.73 (1H, dd, J=8.3 and 4.9 Hz), 6.45 (1H, dd, J=6.0 and 2.6 Hz), 6.88 (1H, d, J=7.8 Hz), 7.22 (1H, t, J=7.8 Hz), 7.28 (1H, d, J=7.8 Hz), 7.29 (1H, s), 7.38 (1H, s), 9.05 (1H, d, J=8.3 Hz, NH), 9.68 (1H, s, OH), 13.15 (1H, br s, CO2H); FDMS m/z 417 (M+), 418 (M+ +1); Anal. Calcd for C18H15N3O5S2 : C, 51.79; H, 3.62; N, 10.07. Found: C, 51.95; H, 3.66; N, 9.80

Sources & evidence

ORD record
ord-e1463ba6939b4679b596bdbe14071bd5
Source dataset
uspto-grants-1997_04
Patent number
US05620968

Reaction notes

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