Trifluoroacetic acid → HCID 131711615, compound

HRID 1382067Notes

Reaction equation

FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1.[CH2:16]([O:19][N:20]=[C:21]([C:45]1[N:46]=[C:47]([NH:50]C(OC(CC)(C)C)=O)[S:48][CH:49]=1)[C:22]([NH:24][CH:25]1[C:43](=[O:44])[N:27]2[C:28]([C:40]([OH:42])=[O:41])=[C:29]([CH2:32][S:33][C:34]3[N:38]([CH3:39])[N:37]=[N:36][N:35]=3)[CH2:30][S:31][C@H:26]12)=[O:23])[CH:17]=[CH2:18]>>[CH2:16]([O:19][N:20]=[C:21]([C:45]1[N:46]=[C:47]([NH2:50])[S:48][CH:49]=1)[C:22]([NH:24][CH:25]1[C:43](=[O:44])[N:27]2[C:28]([C:40]([OH:42])=[O:41])=[C:29]([CH2:32][S:33][C:34]3[N:38]([CH3:39])[N:37]=[N:36][N:35]=3)[CH2:30][S:31][C@H:26]12)=[O:23])[CH:17]=[CH2:18]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 131711616HCID 131711616, compound

Product 1

HCID 131711615HCID 131711615, compoundYield 57.2%

Procedure

Trifluoroacetic acid (4 ml.) and anisole (2 ml.) were added under ice-cooling to 7-[2-allyloxyimino-2-(2-t-pentyloxycarbonylamino-1,3-thiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.9 g.) and the mixture was stirred for 40 minutes at ambient temperature. The reaction mixture was post-treated according to a similar manner to that of Example 17 to give 7-[2-allyloxyimino-2-(2-amino-1,3-thiazol-4-yl)acetamido]-3-(1-methyl-1H-tetrazol-5-yl)thiomethyl-3-cephem-4-carboxylic acid (syn isomer) (0.425 g.).

Workup

additionThe reaction mixture was post-treated

Sources & evidence

ORD record: ord-b0bb60fb9a024addbcc5d1d73da6ffcb
Source dataset: uspto-grants-1989_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04804752

Reaction notes

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