Trifluoroacetic acid → HCID 86741801, compound

HRID 2309399Notes

Reaction equation

HRID 2309399 reaction equation
C([O:5][C:6](=[O:36])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:35])[CH2:13][CH2:14][S:15][C:16](=[O:34])[C@H:17]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26](=[O:33])[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:21]=1)[NH2:18])(C)(C)C.FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[C:26]([C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][CH:23]=1)[CH2:19][C@@H:17]([C:16]([S:15][CH2:14][CH2:13][C:12]([N:8]1[CH2:9][CH2:10][CH2:11][C@H:7]1[C:6]([OH:36])=[O:5])=[O:35])=[O:34])[NH2:18])(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acid2×HCID 86741802HCID 86741802, compound

Product 1

HCID 86741801HCID 86741801, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent2×

Procedure

The product of Example 12 was deprotected by reaction with trifluoroacetic acid in anisole. The reaction mixture was incubated at room temperature for one hour, following which trifluoroacetic acid and anisole were removed in vacuo at 32° C. The reaction mixture was then partitioned between saturated NaHCO3 and ethyl acetate in the cold. The bicarbonate phase was washed twice with ethyl acetate and once with ether. Then, in the presence of ethyl acetate, the bicarbonate phase was acidified with HCl, and, after extraction, the ethyl acetate phase was collected and washed with saturated NaCl, dried over anhydrous MgSO4 and filtered. The solvent was removed under reduced pressure. The product was further purified by chromatography on Sephadex G-25, trademark Pharmacia Company, Uppsala, Sweden, using a 1.2 cm×96 cm column eluted with butanol:acetic acid:water, 4:1:5 (volume ratio). 2.20 me fractions were collected. Most of the product was found in fractions 21 through 23 as determined by positive reaction with o-tolidine/chlorine reagent and with phenazine methosulfate at pH 5.

Workup

  1. customwere removed in vacuo at 32° C
  2. customThe reaction mixture was then partitioned between saturated NaHCO3 and ethyl acetate in the cold
  3. washThe bicarbonate phase was washed twice with ethyl acetate and once with ether
  4. extractionafter extraction
  5. customthe ethyl acetate phase was collected
  6. washwashed with saturated NaCl
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered
  9. customThe solvent was removed under reduced pressure
  10. customThe product was further purified by chromatography on Sephadex G-25, trademark Pharmacia Company, Uppsala, Sweden
  11. washeluted with butanol
  12. custom2.20 me fractions were collected
  13. customas determined by positive reaction with o-tolidine/chlorine reagent and with phenazine methosulfate at pH 5

Sources & evidence

ORD record
ord-b5e9c873e80c4914a165a1d736613b71
Source dataset
uspto-grants-1987_09
Patent number
US04695582

Reaction notes

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