Nitrogen → HCID 86664903, compound

HRID 1189364Notes

Reaction equation

HRID 1189364 reaction equation
N#N.[O:3]=[C:4]([CH3:12])[CH2:5][CH2:6][CH2:7][CH2:8][C:9]([OH:11])=O.CCN(CC)CC.ClC(OCC(C)C)=O.Cl.[CH3:29][O:30][C:31](=[O:36])[C@H:32]([CH2:34][OH:35])[NH2:33]>C1COCC1>[CH3:29][O:30][C:31](=[O:36])[CH:32]([NH:33][C:9](=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][C:4](=[O:3])[CH3:12])[CH2:34][OH:35]

Participants

7

Reactant 5

HCID 947NitrogenHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 988106-Oxoheptanoic acidHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)

Product 1

HCID 86664903HCID 86664903, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of commercially available 6-oxo-heptanoic acid (2.00 g, 13.32 mmol) in THF (82 mL) at −30° C. was treated sequentially with Et3N (3.89 mL, 27.97 mmol) followed by isobutyl chloroformate (1.95 mL, 14.65 mmol). After stirring for 1 h at −30° C., serine methylester hydrochloride (2.32 g, 14.65 mmol was added and the reaction mixture was allowed to warm gradually to rt and stirred for an additional 2 h at rt. The resulting suspension was filtered, the solid washed with THF and the filtrate was concentrated under reduced pressure. Purification of the residue by FC (97:3 EA-MeOH) gave the title compound as a colorless oil. TLC: rf (97:3 EA-MeOH)=0.26. LC-MS-conditions 02: tR=0.56 min [M+H]+=246.44.

Workup

  1. temperatureto warm gradually to rt
  2. stirringstirred for an additional 2 h at rt
  3. filtrationThe resulting suspension was filtered
  4. washthe solid washed with THF
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customPurification of the residue by FC (97:3 EA-MeOH)

Sources & evidence

ORD record
ord-b478c3be65f3420f93d539878205d063
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

Loading…