Trifluoroacetic acid → HCID 131713095, compound

HRID 1995798Notes

Reaction equation

[ClH:1].C([O:6][C:7]([CH2:9][O:10][N:11]=[C:12]([C:38]1[N:39]=[C:40]([NH2:43])[S:41][CH:42]=1)[C:13]([NH:15][CH:16]1[C:36](=[O:37])[N:18]2[C:19]([C:33]([OH:35])=[O:34])=[C:20]([CH2:23][S:24][C:25]3[N:29]([CH2:30][C:31]#[CH:32])[N:28]=[N:27][N:26]=3)[CH2:21][S:22][C@H:17]12)=[O:14])=[O:8])(C)(C)C.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(C)C)(C)C>>[ClH:1].[C:7]([CH2:9][O:10][N:11]=[C:12]([C:38]1[N:39]=[C:40]([NH2:43])[S:41][CH:42]=1)[C:13]([NH:15][CH:16]1[C:36](=[O:37])[N:18]2[C:19]([C:33]([OH:35])=[O:34])=[C:20]([CH2:23][S:24][C:25]3[N:29]([CH2:30][C:31]#[CH:32])[N:28]=[N:27][N:26]=3)[CH2:21][S:22][C@H:17]12)=[O:14])([OH:8])=[O:6]

Participants

Reactant 4

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 7914Diisopropyl Ether

HCID 131713097HCID 131713097, compound

Product 1

HCID 131713095HCID 131713095, compoundYield 95.9%

Procedure

A mixture of 7-[2-tert-butoxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[1-(2-propynyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid hydrochloride (syn isomer) (1.57 g.), anisole (1.57 ml.) and trifluoroacetic acid (8 ml.) was stirred for 3 hours at 10° to 15° C. After the addition of diisopropyl ether to the reaction mixture with stirring, the precipitates were collected by filtration, washed with diisopropyl ether and then dried to give 7-[2-carboxymethoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[1-(2-propynyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid hydrochloride (syn isomer) (1.38 g.)

Workup

stirringwith stirring
filtrationthe precipitates were collected by filtration
washwashed with diisopropyl ether
customdried

Sources & evidence

ORD record: ord-bb88934dc3f44e3eb992d45449aabee2
Source dataset: uspto-grants-1983_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04405617

Reaction notes

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