Trifluoroacetic acid → HCID 131710427, compound

HRID 329239Notes

Reaction equation

[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([NH:9][CH:10]1[C:21](=[O:22])[N:12]2[C:13]([C:18]([O-:20])=[O:19])=[C:14]([CH3:17])[CH2:15][S:16][C@H:11]12)=[O:8].C1([O:29]C)C=CC=CC=1.FC(F)(F)C(O)=O>>[OH:29][CH:6]([C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)[C:7]([NH:9][CH:10]1[C:21](=[O:22])[N:12]2[C:13]([C:18]([OH:20])=[O:19])=[C:14]([CH3:17])[CH2:15][S:16][C@H:11]12)=[O:8]

Participants

Reactant 3

HCID 6422Trifluoroacetic acid

HCID 7519Anisole

HCID 131710428HCID 131710428, compound

Product 1

HCID 131710427HCID 131710427, compoundYield 57.3%

Procedure

Diphenylmethyl (6R,7R,2'R and S)-7-(2'-[fur-2-yl]-acetamido)-3-methylceph-3-em-4-carboxylate (463mg, 1.365 mmole) was treated with anisole and trifluoroacetic acid in the manner described previously [see Example 10 (b)] to give (6R,7R,2'R and S)-7-[2'-hydroxy-2'-(fur-2-yl)acetamido]-3-methylceph-3-em-4-carboxylic acid as a foam (368mg, 1.09 mmole, 57.3%). The title compound was obtained from the acid (368mg, 1.1 mole) by treatment with sodium 2-ethylhexanoate in acetone and ether, as a pale-brown solid containing 21/2mole-equivalents of water (i.r. and microanalysis), (221mg, 0.545 mmole, 50%); λmax (pH6 buffer) 220 and 258nm (ε10,780 and 8,000 respectively); νmax (Nujol) 3370 (OH,NH, and H2O), 1755 (azetidin-2-one), 1675 and 1518 (CONH), and 1590 cm-1 (CO2-); τ(Me2SO-D6) 1.57 and 1.63 (total 1H,2d, J9Hz, NH), 2.37 (1H,s) and 3.59 (2H,m) (furyl protons), 4.44 (1H,m, C7 -H), 4.81 and 4.83 (total 1H, 2s, -CHOH), 4.97 (1H,d,J5Hz, C6 -H), 6.47 and 6.86 (2H,ABq, J18Hz, C2 -H2), 8.00 (3H,s, C3 -CH3). (Found: C, 41.2, 41.5; H,3.4, 3.6; N,6.4, 6.5; S,7.8; Na,5.9. C14H13N2NaO6S.2.5 H2O (405.3) requires: C, 41.6; H,4.5; N,6.9; S,7.9; Na,5.7%).

Sources & evidence

ORD record: ord-f9fc6c14501b43a5a1af180a7fdac42e
Source dataset: uspto-grants-1977_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04020077

Reaction notes

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