Trifluoroacetic acid → HCID 131712426, compound

HRID 1578191Notes

Reaction equation

HRID 1578191 reaction equation
[C:1]1([C@@H:7]([NH:27]C(OC(C)(C)C)=O)[C:8]([NH:10][C@H:11]2[C:18](=[O:19])[N:17]3[C@@H:12]2[CH2:13][CH2:14][CH:15]=[C:16]3[C:20]([O:22]C(C)(C)C)=[O:21])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O>C(Cl)Cl.C1(OC)C=CC=CC=1>[C:1]1([C@@H:7]([NH2:27])[C:8]([NH:10][C@H:11]2[C:18](=[O:19])[N:17]3[C@@H:12]2[CH2:13][CH2:14][CH:15]=[C:16]3[C:20]([OH:22])=[O:21])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131712427HCID 131712427, compound

Product 1

HCID 131712426HCID 131712426, compoundYield 70.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 7519AnisoleSolvent

Procedure

In this Example, 280 mg. (0.59 mmole) of (±)-cis-7-[(R)-2-phenyl-2-t-butyloxycarbonylaminoacetamido]-2-t-butyloxycarbonyl-1-azabicyclo[4,2,0]oct-2-en-8-one obtained in Example 25 is dissolved in 2.5 ml of anhydrous methylene chloride and 2.5 ml of anisole, and 5.0 ml of trifluoroacetic acid is added under ice cooling. The mixture is allowed to stand for 4 hours and 50 minutes under ice cooling and is then concentrated. To the concentrated residue, 10 ml of ether is added and the mixture is stirred at room temperature for one hour to form a precipitate. The precipitate is collected by filtration to obtain 202 mg. (70.9%) of the desired compound as a pale yellow powder having the following properties.

Workup

  1. concentrationis then concentrated
  2. additionTo the concentrated residue, 10 ml of ether is added
  3. customto form a precipitate
  4. filtrationThe precipitate is collected by filtration
  5. customto obtain 202 mg

Sources & evidence

ORD record
ord-d76288d8300f491a996020395df5a4e7
Source dataset
uspto-grants-1981_09
Patent number
US04291164

Reaction notes

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