Trifluoroacetic acid → HCID 178508514, compound

HRID 2214770Notes

Reaction equation

FC(F)(F)C(O)=O.C([SiH](CC)CC)C.C1(C([O:28][C:29]([C:31]2[N:32]3[CH:35]([CH2:36][CH2:37][C:38]=2[S:39][C:40]2[S:41][CH:42]=[N:43][N:44]=2)[C@@H:34]([NH:45][C:46](=[O:76])/[C:47](/[C:69]2[N:70]=[C:71]([NH2:75])[S:72][C:73]=2[Cl:74])=[N:48]\[O:49]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[C:33]3=[O:77])=[O:30])C2C=CC=CC=2)C=CC=CC=1>ClCCl>[NH2:75][C:71]1[S:72][C:73]([Cl:74])=[C:69](/[C:47](=[N:48]/[OH:49])/[C:46]([NH:45][C@H:34]2[C:33](=[O:77])[N:32]3[CH:35]2[CH2:36][CH2:37][C:38]([S:39][C:40]2[S:41][CH:42]=[N:43][N:44]=2)=[C:31]3[C:29]([OH:30])=[O:28])=[O:76])[N:70]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of trifluoroacetic acid (5 mL), triethylsilane (3 mL) and dichloromethane (8 mL) was cooled to 0° C. and (7R)-7-[(Z)-2-(2-amino-5-chlorothiazol-4-yl)-2-(triphenylmethoxyimino]acetamido]-3-[1,3,4-thiadiazol-2-ylthio]-8-oxo-1-aza-bicyclo-[4.2.0]oct-2-ene-2-carboxylate diphenylmethyl ester (1.5 g) was added in portions. The reaction mixture was stirred at 0° C. for 3 hours, was allowed to warm up to room temp. and was evaporated to dryness. The residue was treated with diethyl ether (50 mL), and the solid that formed was filtered and dried to give the crude product. The crude product was purified on HP 20 initially with water elution until the pH was neutral, and thereafter with acetonitrile:water 80:20 to give the title compound (0.63 g.)

Workup

temperatureto warm up to room temp.
customwas evaporated to dryness
additionThe residue was treated with diethyl ether (50 mL)
customthe solid that formed
filtrationwas filtered
customdried
customto give the crude product
customThe crude product was purified on HP 20 initially with water elution until the pH

Sources & evidence

ORD record: ord-802bc00aee8a4f5784405f15d22fabe7
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109190B2

Reaction notes

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