Trifluoroacetic acid → (6R)-trans-3-chloromethyl-7-[(2,5-dichlorophenyl)thioacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

HRID 53610Notes

Reaction equation

C1(C([O:14][C:15]([C:17]2[N:18]3[C@H:21]([S:22][CH2:23][C:24]=2[CH2:25][Cl:26])[C@H:20]([NH:27][C:28](=[S:38])[CH2:29][C:30]2[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=2[Cl:37])[C:19]3=[O:39])=[O:16])C2C=CC=CC=2)C=CC=CC=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:26][CH2:25][C:24]1[CH2:23][S:22][C@H:21]2[N:18]([C:19](=[O:39])[C@H:20]2[NH:27][C:28](=[S:38])[CH2:29][C:30]2[CH:35]=[C:34]([Cl:36])[CH:33]=[CH:32][C:31]=2[Cl:37])[C:17]=1[C:15]([OH:16])=[O:14]

Participants

Conditions

Temperature: 0 °C

Procedure

A slurry of (6R)-trans-3-chloromethyl-7-[(2,5-dichlorophenyl)thioacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate diphenylmethyl ester (10.0 g, 15.8 mmol) in CH2Cl2 (200 mL) at 0° C. was treated with anisole (24 mL) and then trifluoroacetic acid (80 mL). The resulting solution was stirred for 1 h at 0° C. and then concentrated under reduced pressure. The residue was stirred with Et2O, and the resulting solid was collected by filtration to give 5.20 g of (6R)-trans-3-chloromethyl-7-[(2,5-dichlorophenyl)-thioacetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid as a white solid (70% yield), m.p. 125° C. 1H NMR (300 MHz, DMSO-d6) δ3.51 (d, J=18 Hz, 1H), 3.70 (d, J=18 Hz, 1H), 3.91 (s, 2H), 4.52 (d, J=11 Hz, 1H), 4.58 (d, J=11 Hz, 1H), 5.13 (d, J=5 Hz, 1H), 5.70 (dd, J=5, 8 Hz, 1H), 7.24 (dd, J=2, 8 Hz, 1H), 7.47 (dd, J=2, 8 Hz, 2H), 9.28 (d, J=8 Hz, 1H).

Workup

concentrationconcentrated under reduced pressure
stirringThe residue was stirred with Et2O
filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record: ord-26e02884ae3a46a8aebbb1e7daf48c61
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05620969

Reaction notes

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