Trifluoroacetic acid → HCID 131714081, compound

HRID 2412518Notes

Reaction equation

[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18]3[N:19]([CH2:23][CH2:24][CH2:25][C:26]([O:28]C(C)(C)C)=[O:27])[CH:20]=[CH:21][N:22]=3)[C:15](=[O:33])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2].C(O)(C(F)(F)F)=O>>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[CH:16]([NH:17][C:18]3[N:19]([CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH:20]=[CH:21][N:22]=3)[C:15](=[O:33])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 70472209HCID 70472209, compound

Product 1

HCID 131714081HCID 131714081, compound

Procedure

3-Acetoxymethyl-7-[1-(3-t-butoxycarbonylpropyl)imidazol-2-yl]aminoceph-3-em-4-carboxylic acid was treated with TFA according to the process of Example 39, except that product was isolated by trituration, to give 3-acetoxymethyl-7-[1-(3-carboxypropyl)imidazol-2-yl]amino ceph-3-em-4-carboxylic acid, having the following n.m.r. spectrum in d6DMSO+CD3CO2D: 1.6-2.4 (m, 4H); 2.0 (s, 3H); 3.5 (d, 1H); 3.7 (d, 1H); 4.0 (t, 2H); 4.7 (d, 1H); 5.0 (d, 1H); 5.2 (d, 1H); 5.6 (s, 1H); 7.1 (m, 2H).

Workup

customwas isolated by trituration

Sources & evidence

ORD record: ord-170ed8c24c49418c8ca15e4700526546
Source dataset: uspto-grants-1985_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04492692

Reaction notes

Loading…