Trifluoroacetic acid → HCID 20443645, compound

HRID 1632320Notes

Reaction equation

HRID 1632320 reaction equation
C1(OC)C=CC=CC=1.[C:9]([O:13][C:14]([CH:16]([O:23]/[N:24]=[C:25](/[C:42]1[N:43]=[C:44]([NH:47][C:48]([C:61]2[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=2)([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[S:45][CH:46]=1)\[C:26]([O:28]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:27])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15])([CH3:12])([CH3:11])[CH3:10].FC(F)(F)C(O)=O>C(Cl)Cl>[C:9]([O:13][C:14]([CH:16]([O:23]/[N:24]=[C:25](/[C:42]1[N:43]=[C:44]([NH:47][C:48]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)([C:61]2[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=2)[C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)[S:45][CH:46]=1)\[C:26]([OH:28])=[O:27])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 145802559HCID 145802559, compound

Product 1

HCID 20443645HCID 20443645, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

To a mixture of 4 ml of methylene dichloride and 1 ml of anisole was added 2.61 g (0.0033 mole) of benzhydryl (Z)-2-(α-tert-butoxycarbonylbenzyloximino)-2-(2-tritylaminothiazol-4-yl)acetate and after cooling the mixture to -30° C., 3 ml of trifluoroacetic acid was added dropwise to the mixture at a temperature below -20° C. over a period of 5 minutes. Thereafter, the mixture was maintained for one hour at -20° C. to -15° C. and then, methylene dichloride and trifluoroacetic acid were distilled off at low temperature under reduced pressure to provide an oily product. The oily product was subjected to silica gel column chromatography, eluted with a mixture of chloroform, isopropyl alcohol, and formic acid (90:10:2), the fractions containing the desired product were collected, and the solvents were distilled off to provide 1.15 g (Z)-(α-tert-butoxycarbonylbenzyloximino)-2-(2-tritylaminothiazol-4-yl)acetic acid.

Workup

  1. temperatureThereafter, the mixture was maintained for one hour at -20° C. to -15° C.
  2. distillationmethylene dichloride and trifluoroacetic acid were distilled off at low temperature under reduced pressure
  3. customto provide an oily product
  4. washeluted with a mixture of chloroform, isopropyl alcohol, and formic acid (90:10:2)
  5. additionthe fractions containing the desired product
  6. customwere collected
  7. distillationthe solvents were distilled off

Sources & evidence

ORD record
ord-a6ad02fd65b44daab19280c3167dfd8d
Source dataset
uspto-grants-1984_10
Patent number
US04474779

Reaction notes

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