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

HRID 53587Notes

Reaction equation

HRID 53587 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]=3O)[S:20][CH:21]=2)[C:7]=1[C:31]([OH:33])=[O:32])(=[O:3])[CH3:2].[SiH](CC)(CC)CC.FC(F)(F)C(O)=[O:44]>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]=[C:24]([OH:44])[CH:23]=3)[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 731922363-[(Acetyloxy)methyl]-7-[[[2-(3-hydroxyphenyl)-4-thiazolyl]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic AcidYield 96%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

The procedure used for the preparation of 9a was repeated with 8m (157 mg, 0.240 mmol), Et3SiH (0.383 mL, 2.40 mmol), and trifluoroacetic acid (0.739 mL, 9.59 mmol) in dry ClCH2CH2Cl (6 mL) at 0° C. under nitrogen to give 9m (113 mg, 96%) as a white solid after crystallization from THF/CH2Cl2 /hexane. mp 140° C. (dec); IR (KBr) 3600-2650 (br), 3286, 1782, 1738, 1671, 1230 cm-1 ; 1H NMR (DMSO-d6) δ1.98 (3H, s, CH3), 3.44 (1H, d, J=18.1 Hz), 3.59 (1H, d, J=18.1 Hz), 3.72 (2H, s, CH2), 4.64 (1H, d, J=12.8 Hz), 4.96 (1H, d, J=12.8 Hz), 5.07 (1H, d, J=4.8 Hz), 5.69 (1H, dd, J=8.2 and 4.8 Hz), 6.82 (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), 7.39 (1H, s), 9.06 (1H, d, J=8.2 Hz, NH), 9.68 (1H, br s, OH), 13.62 (1H, br s, CO2H); FDMS m/z 490 (M+ +1); Anal. Calcd for C21H19N3O7S2.(C4H8O) 0.25: C, 52.06; H, 4.17; N, 8.28. Found: C, 51.95; H, 3.94; N, 8.04

Sources & evidence

ORD record
ord-0e1cbab3d3be49bf97a887f50a3028e5
Source dataset
uspto-grants-1997_04
Patent number
US05620968

Reaction notes

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