Trifluoroacetic acid → HCID 12851208, compound

HRID 1446983Notes

Reaction equation

HRID 1446983 reaction equation
C(O[C:6]([NH:8][C@@H:9]([C:18](=[O:20])[NH2:19])[CH2:10][CH2:11][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[O:13])=[O:7])(C)(C)C.FC(F)(F)C(O)=O.[C:28]([O:32][C:33]([NH:35][C@H:36](C(O)=O)[CH2:37][O:38][CH2:39][C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>>[C:28]([O:32][C:33]([NH:35][C@H:36]([C:6]([NH:8][C@@H:9]([C:18](=[O:20])[NH2:19])[CH2:10][CH2:11][C:12]([O:14][CH:15]([CH3:16])[CH3:17])=[O:13])=[O:7])[CH2:37][O:38][CH2:39][C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 90234L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-HCID 13190126HCID 13190126, compound

Product 1

HCID 12851208HCID 12851208, compound

Procedure

Isopropyl t-butyloxycarbonyl-D-isoglutaminate (176 mg, 0.61 mmol) was treated with trifluoroacetic acid (1 ml) at room temperature for 20 minutes. Trifluoroacetic acid was evaporated and the residue was washed thoroughly with a mixture of diethyl ether-petroleum ether (1:1) and dried in a desiccator over sodium hydroxide pellets. The resulting trifluoroacetic acid salt was dissolved in acetonitrile (10 ml) together with triethylamine (0.19 ml). To this solution was added t-butyloxycarbonyl-O-benzyl-L-serine HOSuc ester (274 mg, 0.7 mmol), and the mixture was allowed to react for 15 hours at room temperature. The solvent was evaporated and the residue was dissolved in ethyl acetate (20 ml). The solution was washed successively with a 5% aqueous sodium bicarbonate solution, 1 N hydrochloric acid and water, dried over anhydrous sodium sulfate, and evaporated. The residue was crystallized by addition of petroleum ether and the resulting crystals were filtered to obtain isopropyl t-butyloxycarbonyl-O-benzyl-L-seryl-D-isoglutaminate (243 mg). Melting point, 98°-99° C. [α]D22 +2.0° (c 0.5, DMF). Rf2 =0.50; Rf3 =0.78.

Workup

  1. customTrifluoroacetic acid was evaporated
  2. washthe residue was washed thoroughly with a mixture of diethyl ether-petroleum ether (1:1)
  3. dry with materialdried in a desiccator over sodium hydroxide pellets
  4. dissolutionThe resulting trifluoroacetic acid salt was dissolved in acetonitrile (10 ml) together with triethylamine (0.19 ml)
  5. customto react for 15 hours at room temperature
  6. customThe solvent was evaporated
  7. dissolutionthe residue was dissolved in ethyl acetate (20 ml)
  8. washThe solution was washed successively with a 5% aqueous sodium bicarbonate solution, 1 N hydrochloric acid and water
  9. dry with materialdried over anhydrous sodium sulfate
  10. customevaporated
  11. customThe residue was crystallized by addition of petroleum ether
  12. filtrationthe resulting crystals were filtered

Sources & evidence

ORD record
ord-e8f757e486c2433aad8fd871f0a5d926
Source dataset
uspto-grants-1982_02
Patent number
US04314998

Reaction notes

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