Tetrahydrofuran → HCID 91582719, compound

HRID 1743251Notes

Reaction equation

HRID 1743251 reaction equation
[C:1]([C@@H:4]1[CH2:8][S:7][C@H:6]2[CH2:9][C@@H:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[C:11](=[O:12])[N:5]12)(=O)[NH2:2].[CH2:21](N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH2:41]1[CH2:45]OC[CH2:42]1>>[C:1]([C@@H:4]1[CH2:8][S:7][C@H:6]2[CH2:9][C@:10]([NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])([CH2:21][CH:41]([CH3:42])[CH3:45])[C:11](=[O:12])[N:5]12)#[N:2]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 21587862HCID 21587862, compound

Product 1

HCID 91582719HCID 91582719, compound

Procedure

The crude product from 2e was dissolved in 5 ml of THF. 63 μl of triethylamine and 29 μl of trifluoroacetic anhydride were added thereto. The mixture was stirred at room temperature for 3 h and then partitioned between 60 ml of water and 60 ml of ethyl acetate. The aqueous phase was extracted twice with 50 ml of ethyl acetate each time, and the combined organic phases were dried with MgSO4. The solvents were removed in vacuo and the residue was purified by chromatography on silica gel.

Workup

  1. custompartitioned between 60 ml of water and 60 ml of ethyl acetate
  2. extractionThe aqueous phase was extracted twice with 50 ml of ethyl acetate each time
  3. dry with materialthe combined organic phases were dried with MgSO4
  4. customThe solvents were removed in vacuo
  5. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-429eac9b5f1a4c4fbae62979a88cc8d6
Source dataset
uspto-grants-2006_03
Patent number
US07008957B2

Reaction notes

Loading…