Trifluoroacetic acid → HCID 178477398, compound

HRID 1658197Notes

Reaction equation

HRID 1658197 reaction equation
[NH2:1][CH:2]1[C:24](=[O:25])[N:4]2[C:5]([C:17]([O:19]C(C)(C)C)=[O:18])=[C:6]([CH:9]([S:11][C:12]3[NH:16][N:15]=[N:14][N:13]=3)[CH3:10])[CH2:7][S:8][C@H:3]12.[C:26]([CH2:28][S:29]([CH2:32][C:33](O)=[O:34])(=[O:31])=[O:30])#[N:27].C1(N=C=NC2CCCCC2)CCCCC1.FC(F)(F)C(O)=O>>[C:26]([CH2:28][S:29]([CH2:32][C:33]([NH:1][CH:2]1[C:24](=[O:25])[N:4]2[C:5]([C:17]([OH:19])=[O:18])=[C:6]([CH:9]([S:11][C:12]3[NH:13][N:14]=[N:15][N:16]=3)[CH3:10])[CH2:7][S:8][C@H:3]12)=[O:34])(=[O:31])=[O:30])#[N:27]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 23470093Cyanomethylsulfonylacetic acidHCID 178477375HCID 178477375, compound

Product 1

HCID 178477398HCID 178477398, compound

Procedure

t-Butyl 7-amino-3-(1-methyltetrazol-5-ylthiomethyl)-3-cephem-4-carboxylate (5.75 g, 15 mmol), cyanomethylsulfonylacetic acid (2.45 g, 15 mmol), and dicyclohexylcarbodiimide (3.1 g, 15 mmol) were reacted as in Example 6. The t-butyl ester was treated with trifluoroacetic acid for 20 minutes as in Example 6, to give the title compound.

Sources & evidence

ORD record
ord-f8e74e11928b41b5b3afab8070176eb7
Source dataset
uspto-grants-1976_06
Patent number
US03963711

Reaction notes

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