Trifluoroacetic acid → HCID 131711677, compound

HRID 2052177Notes

Reaction equation

[CH3:1][O:2][N:3]=[C:4]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:5]([NH:7][CH:8]1[C:37](=[O:38])[N:10]2[C:11]([C:21]([O:23]C(C3C=CC=CC=3)C3C=CC=CC=3)=[O:22])=[C:12]([C:15]3[S:16][C:17]([CH3:20])=[N:18][N:19]=3)[CH2:13][S:14][C@H:9]12)=[O:6].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>>[CH3:1][O:2][N:3]=[C:4]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:5]([NH:7][CH:8]1[C:37](=[O:38])[N:10]2[C:11]([C:21]([OH:23])=[O:22])=[C:12]([C:15]3[S:16][C:17]([CH3:20])=[N:18][N:19]=3)[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 131711678HCID 131711678, compound

Product 1

HCID 131711677HCID 131711677, compoundYield 89.5%

Procedure

A mixture of 0.07 g of benzhydryl 7-(2-methoxyimino-2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylate (obtained in Example 59), 2 ml of anisole and 4 ml of trifluoroacetic acid is stirred for 30 minutes at room temperature. After removal of the solvent under reduced pressure, the residue is triturated with the addition of absolute ether. The precipitates are filtered, and washed with ether to give 0.046 g of 7-(2-methoxyimino-2-phenylacetamido)-3-(5-methyl-1,3,4-thiadiazol-2-yl)-3-cephem-4-carboxylic acid.

Workup

customAfter removal of the solvent under reduced pressure
customthe residue is triturated with the addition of absolute ether
filtrationThe precipitates are filtered
washwashed with ether

Sources & evidence

ORD record: ord-529fe59995b040d28c37f586ae2a7fbc
Source dataset: uspto-grants-1980_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04182866

Reaction notes

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