Trifluoroacetic acid → HCID 131711801, compound

HRID 1707180Notes

Reaction equation

HRID 1707180 reaction equation
[C:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:20]([NH:21][C:22](=[O:36])[C:23]([C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)=[N:24][O:25][C:26](=[O:30])[CH:27]([Cl:29])[Cl:28])[C:19](=[O:37])[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:1]([O:4][CH2:5][C:6]1[CH2:7][S:8][C@@H:9]2[C@H:20]([NH:21][C:22](=[O:36])[C:23](=[N:24][O:25][C:26](=[O:30])[CH:27]([Cl:29])[Cl:28])[C:31]3[S:32][CH:33]=[CH:34][CH:35]=3)[C:19](=[O:37])[N:10]2[C:11]=1[C:12]([OH:14])=[O:13])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131711800HCID 131711800, compound

Product 1

HCID 131711801HCID 131711801, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

A solution of t-butyl 3-acetoxymethyl-7β-[2-dichloroacetoxyimino-(thien-2-yl)acetamido]ceph-3-em-4-carboxylate (syn-isomer) in anisole (20 ml.) was treated with trifluoroacetic acid (100 ml.). After 5 minutes at 20° the solution was concentrated under reduced pressure at 35°. Ethyl acetate was added and the solution was again concentrated, whereupon a solid separated out. Ethyl acetate was evaporated from the residue three more times and the solid was collected and washed with ether to give 3-acetoxymethyl-7β-[2-dichloroacetoxyimino-2-(thien-2-yl)acetamido]ceph-3-em-4-carboxylic acid (syn-isomer) (37 g., 53%) λmax. (ethanol) 263 nm (ε14,800), τ(DMSO-d6) values include -0.19 (doublet, J 8 Hz; NH), 3.02 (singlet, CHCl2), 7.94 (singlet, OCOCH3).

Workup

  1. concentrationAfter 5 minutes at 20° the solution was concentrated under reduced pressure at 35°
  2. additionEthyl acetate was added
  3. concentrationthe solution was again concentrated, whereupon a solid
  4. customseparated out
  5. customEthyl acetate was evaporated from the residue three more times
  6. customthe solid was collected
  7. washwashed with ether

Sources & evidence

ORD record
ord-f6800411f2c74b2fadf867a9409829e4
Source dataset
uspto-grants-1980_06
Patent number
US04209616

Reaction notes

Loading…