Trifluoroacetic acid → HCID 13175970, compound

HRID 2413412Notes

Reaction equation

C([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[C:25]1[S:29][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:27][CH:26]=1)[CH:20]([NH:36]C(OC(C)(C)C)=O)[C:19]2=[O:44])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.FC(F)(F)C(O)=O>>[NH2:36][CH:20]1[C:19](=[O:44])[N:18]2[CH:21]1[S:22][CH2:23][C:24]([C:25]1[S:29][C:28]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[N:27][CH:26]=1)=[C:17]2[C:15]([OH:16])=[O:14]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 13175940HCID 13175940, compound

Product 1

HCID 13175970HCID 13175970, compoundYield 100.8%

Procedure

2-Benzhydryloxycarbonyl-7-t-butoxycarbonylamino-8-oxo-3-(2-phenyl-thiazol-5-yl)-5-thia-1-azabicyclo[4.2.0]-oct-2-ene (5.7 g) is treated with trifluoroacetic acid (57 cc) for 20 minutes at 20° C. and the reaction mixture is then concentrated to dryness under reduced pressure (0.2 mm Hg; 0.03 kPa) at 30° C. The residue is taken up in ethyl acetate (100 cc), which is evaporated under reduced pressure (30 mm Hg; 4 kPa) at 30° C. This residue is triturated with isopropyl ether (100 cc). The solid is filtered off, washed with isopropyl ether (3×50 cc) and dried under reduced pressure (0.2 mm Hg; 0.03 kPa) at 20° C. 7-Amino-2-carboxy-8-oxo-3-(2-phenyl-thiazol-5-yl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene (3.3 g) is obtained in the form of an ochre solid.

Workup

concentrationthe reaction mixture is then concentrated to dryness under reduced pressure (0.2 mm Hg; 0.03 kPa) at 30° C
customwhich is evaporated under reduced pressure (30 mm Hg; 4 kPa) at 30° C
customThis residue is triturated with isopropyl ether (100 cc)
filtrationThe solid is filtered off
washwashed with isopropyl ether (3×50 cc)
customdried under reduced pressure (0.2 mm Hg; 0.03 kPa) at 20° C

Sources & evidence

ORD record: ord-841a861d7bfb4a9f91a0ebc3fadd13dc
Source dataset: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04496560

Reaction notes

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