反応 #6388

反応方程式

t-Butyl (6R,7R)-3-[(5S)-2-oxotetrahydrofuran-5-yl]-7-[2-(2-tritylaminothiazol-4-yl)-2-(Z)-trityloxyiminoacetamido]ceph-3-em-4-carboxylate

→

(6R,7R)-7-[2-(2-Aminothiazol-4-yl)-2-(Z)-hydroxyiminoacetamido]-3-[(5RS)-2-oxotetrahydrofuran-5-yl)ceph-3-em-4-carboxylic acid

溶媒

hydrochloric acid

hydrochloric acid

formic acid

反応条件

後処理

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for a further 0.5 h
3. 3
   ろ過The precipitate was filtered off
4. 4
   洗浄washed with 90% formic acid
5. 5
   その他the filtrate was evaporated to dryness
6. 6
   洗浄washed with ether and freeze
7. 7
   その他dried
8. 8
   その他The crude product (0.153 g) was chromatographed on HP20SS
9. 9
   洗浄eluting with 0,2,4,6% THF in water
10. 10
    workup.ADDITIONFractions containing the title compound
11. 11
    濃縮concentrated
12. 12
    乾燥freeze dried (41 mg, 40%), νmax (KBr) 1764, 1664, 1609, 1529, 1389 and 1184 cm-1

実験手順

t-Butyl (6R,7R)-3-[(5S)-2-oxotetrahydrofuran-5-yl]-7-[2-(2-tritylaminothiazol-4-yl)-2-(Z)-trityloxyiminoacetamido]ceph-3-em-4-carboxylate (0.22 g) was dissolved in 0.1M hydrochloric acid in 90% formic acid (2.5 ml) and stirred for 1 h. Concentrated hydrochloric acid (0.1 ml) was added and stirring was continued for a further 0.5 h. The precipitate was filtered off, washed with 90% formic acid, and the filtrate was evaporated to dryness. The residue in water was adjusted to pH3 with solid potassium carbonate, washed with ether and freeze dried. The crude product (0.153 g) was chromatographed on HP20SS, eluting with 0,2,4,6% THF in water. Fractions containing the title compound were combined, concentrated and freeze dried (41 mg, 40%), νmax (KBr) 1764, 1664, 1609, 1529, 1389 and 1184 cm-1 ; δH (D2O) 2.1-2.8 (4H,m , 3.37 and 3.63, 3.39 and 3.53 (2H,2ABq,J17.5,17.8 Hz), 5.21, 5.23 (1H,2d, J4.6 Hz), 5.5-5.65 (1H,m), 5.82 (1H,d,J4.6 Hz), 6.95 (1H,s); [mass spectrum: + ve ion (thioglyerol) MH+, 454].

出典