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

HRID 53589Notes

Reaction equation

HRID 53589 reaction equation
[C:1]([O:4][CH2:5][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:3])[CH3:2].[SiH](CC)(CC)[CH2:35]C.FC(F)(F)C(O)=O>C(Cl)CCl>[C:1]([O:4][CH2:5][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[O:28][CH3:35])[S:20][CH:21]=2)[C:7]=1[C:31]([OH:33])=[O:32])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 136381123HCID 136381123, compound

Product 1

HCID 731922383-[(Acetyloxy)methyl]-7-[[[2-(2-methoxyphenyl)-4-thiazolyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic AcidYield 73%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The procedure used for the preparation of 9a was repeated with 8o (193 mg, 0.288 mmol), Et3SiH (0.461 mL, 2.88 mmol), and trifluoroacetic acid (0.887 mL, 11.5 mmol) in dry ClCH2CH2Cl (7 mL) at 0° C. under nitrogen to give 9o (106 mg, 73%) as a white solid after crystallization from THF/CH2Cl2 /hexane. mp 178° C. (dec); IR (KBr) 3550-2800 (br), 3278, 1785, 1735, 1667, 1256 cm-1 ; 1H NMR (DMSO-d6) δ1.98 (3H, s, CH3), 3.45 (1H, d, J=18.1 Hz), 3.59 (1H, d, J=18.1 Hz), 3.74 (2H, s, CH2), 3.96 (3H, s, CH3), 4.65 (1H, d, J=12.8 Hz), 4.96 (1H, d, J=12.8 Hz), 5.07 (1H, d, J=4.8 Hz), 5.71 (1H, dd, J=8.1 and 4.8 Hz), 7.04 (1H, t, J=7.5 Hz), 7.19 (1H, d, J=8.3 Hz), 7.37-7.42 (1H, m), 7.41 (1H, s), 8.22 (1H, d, J=7.5 Hz), 9.06 (1H, d, J=8.1 Hz, NH), 13.62 (1H, br s, CO2H); FDMS m/z 504 (M+ +1); Anal. Calcd for C22H21N3O7S2 : C, 52.48; H, 4.20; N, 8.34. Found: C, 52.72; H, 4.27; N, 8.10

Sources & evidence

ORD record
ord-38fb2891e85542e888be10595f56b00d
Source dataset
uspto-grants-1997_04
Patent number
US05620968

Reaction notes

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