Trifluoroacetic acid → HCID 88823815, compound

HRID 435992Notes

Reaction equation

HRID 435992 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@:20]([O:51][CH3:52])([NH:21][C:22](=[O:50])[C:23](=[N:29][O:30]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:24]3[O:25][CH:26]=[CH:27][CH:28]=3)[C:19](=[O:53])[N:10]2[C:11]=1[C:12]([O:14]C(C)(C)C)=[O:13])(=[O:3])[CH3:2].FC(F)(F)C(O)=O.C1(OC)C=CC=CC=1>C(=O)(O)[O-].[Na+]>[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@@:20]([NH:21][C:22](=[O:50])[C:23](=[N:29][OH:30])[C:24]3[O:25][CH:26]=[CH:27][CH:28]=3)([O:51][CH3:52])[C:19](=[O:53])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 131710641HCID 131710641, compound

Product 1

HCID 88823815HCID 88823815, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

t-Butyl (6R,7S)-3-acetoxymethyl-7-methoxy-7-[2-triphenylmethoxyimino-2-(fur-2-yl)-acetamido]-ceph-3-em-4-carboxylate (syn isomer) (713.3 mg, 0.966 mmole) was treated with trifluoroacetic acid (10 ml) and anisole (5 ml) for a total of 40 mins. and then added slowly to rapidly stirred saturated aqueous sodium bicarbonate (600 ml.). The mixture was extracted with ethyl acetate (2×150 ml), covered with ethyl acetate (200 ml), and adjusted to pH 2 with orthophosphoric acid. The organic layer was combined with the ethyl acetate wash (200 ml) of the aqueous layer, dried, and evaporated to a brown foam. Chromatography on three 40 × 20 cm. preparative-layer plates in chloroform-methanol-formic acid (90:16:2) provided a sample of the title compound as a pale-yellow foam containing ca 21/2 mole-equivalents water (i.r. and microanalysis) (137 mg, 0.283 mmole, 29%) paper chromatography Rf 0.26, Rf/Rf cephaloram 0.58, λmax (pH 6 buffer) 272.5 nm (ε 16,400).

Workup

  1. extractionThe mixture was extracted with ethyl acetate (2×150 ml)
  2. washwash (200 ml) of the aqueous layer
  3. customdried
  4. customevaporated to a brown foam

Sources & evidence

ORD record
ord-d16f8faadc3d4f33aa70fc80d495e601
Source dataset
uspto-grants-1977_02
Patent number
US04007174

Reaction notes

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