Triethylamine → HCID 69095085, compound

HRID 2196512Notes

Reaction equation

HRID 2196512 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[S:15][C:14]([CH2:16][NH2:17])=[CH:13][CH:12]=2)[N:9]=[C:8]([C:18]([F:21])([F:20])[F:19])[CH:7]=1.[NH:22]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[C@H:23]([C:25](ON1C(=O)CCC1=O)=[O:26])[CH3:24].C(N(CC)CC)C>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[N:10]([C:11]2[S:15][C:14]([CH2:16][NH:17][C:25](=[O:26])[C@@H:23]([NH:22][C:35](=[O:36])[O:37][C:38]([CH3:40])([CH3:39])[CH3:41])[CH3:24])=[CH:13][CH:12]=2)[N:9]=[C:8]([C:18]([F:20])([F:21])[F:19])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11011585Boc-Ala-OSuHCID 59843250HCID 59843250, compound

Product 1

HCID 69095085HCID 69095085, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 23 (crude) (0.588 mmol) in CH2Cl2 (2.9 mL) at 0 degrees were added Boc-Ala-OSu (185 mg, 0.647 mmol) and triethylamine (0.18 mL, 1.3 mmol). The mixture was allowed to reach 21° C. slowly, stirring for 16 h at room temperature. The solvent was then evaporated. The mixture was quenched with a saturated ammonium chloride solution and extracted with ethyl acetate, washed with brine, dried (MgSO4) filtered and concentrated. The residue was purified by silica gel column chromatography with gradient of EtOAc (20-60%) in hexanes to afford 24 (140 mg, 49%) as a white solid. LRMS (ESI): calc. 484.1; found 507.2 (MNa)+.

Workup

  1. customto reach 21° C.
  2. customThe solvent was then evaporated
  3. customThe mixture was quenched with a saturated ammonium chloride solution
  4. extractionextracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by silica gel column chromatography with gradient of EtOAc (20-60%) in hexanes

Sources & evidence

ORD record
ord-d0a0119f2b75459a906fa248a9c0b6a3
Source dataset
uspto-grants-2012_12
Patent number
US08338437B2

Reaction notes

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