Trifluoroacetic acid → HCID 86585656, compound

HRID 1358914Notes

Reaction equation

C([O:14][C:15]([C:17]1[N:18]2[CH:21]([S:22][CH2:23][C:24]=1[S:25][C:26]1[S:27][C:28]([NH2:31])=[N:29][N:30]=1)[C@H:20]([NH:32][C:33](=[O:63])[C:34]([C:56]1[N:57]=[C:58]([NH2:62])[S:59][C:60]=1[Cl:61])=[N:35][O:36]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:19]2=[O:64])=[O:16])(C1C=CC=CC=1)C1C=CC=CC=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[NH2:62][C:58]1[S:59][C:60]([Cl:61])=[C:56]([C:34](=[N:35][OH:36])[C:33]([NH:32][C@@H:20]2[C:19](=[O:64])[N:18]3[CH:21]2[S:22][CH2:23][C:24]([S:25][C:26]2[S:27][C:28]([NH2:31])=[N:29][N:30]=2)=[C:17]3[C:15]([OH:16])=[O:14])=[O:63])[N:57]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (7R)-7-[2-(2-amino-5-chloro-thiazol-4-yl)-2-trityloxyiminoacetylamino ]-3-(5-amino-[1,3,4]thiadiazol-2-ylsulfanyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (150 mg, 0.17 mmol) in dichloromethane (7.5 mL) was added triethylsilane (1.5 mL). The mixture was cooled to 0° C. and trifluoroacetic acid (7.5 mL) was added. After 2 hr at 0° C. the reaction mixture was concentrated under vacuum and disopropyl ether was added to the oily residue. The title compound precipitated and was filtered, washed with additional diisopropyl ether and dried under vacuum (85 mg, 65%).

Workup

concentrationAfter 2 hr at 0° C. the reaction mixture was concentrated under vacuum and disopropyl ether
additionwas added to the oily residue
customThe title compound precipitated
filtrationwas filtered
washwashed with additional diisopropyl ether
customdried under vacuum (85 mg, 65%)

Sources & evidence

ORD record: ord-a7e8039dde2b4566948e5386ad4df3d2
Source dataset: uspto-grants-2003_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06599893B2

Reaction notes

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