Triethylamine → HCID 88884668, compound

HRID 2369468Notes

Reaction equation

HRID 2369468 reaction equation
[CH2:1]([O:4][C:5](=[O:17])[C@H:6]([CH2:15][OH:16])[NH:7][C:8]([O:10]C(C)(C)C)=O)[CH:2]=[CH2:3].C1C(=O)N(OC([CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34]2[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][C:35]=2[N+:43]([O-:45])=[O:44])=O)C(=O)C1.C(N(CC)CC)C>Cl.O1CCOCC1>[CH2:1]([O:4][C:5](=[O:17])[C@H:6]([CH2:15][OH:16])[NH:7][C:8](=[O:10])[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][NH:33][C:34]1[CH:39]=[CH:38][C:37]([N+:40]([O-:42])=[O:41])=[CH:36][C:35]=1[N+:43]([O-:45])=[O:44])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11356996N-t-Boc-L-serine Allyl EsterHCID 162171391-{[6-(2,4-Dinitroanilino)hexanoyl]oxy}pyrrolidine-2,5-dione

Product 1

HCID 88884668HCID 88884668, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

A solution of N-(tert-butoxycarbonyl)-L-serine allyl ester (0.175 g, 0.731 mmol) in 4 M hydrogen chloride/dioxane (2 mL) was stirred at ambient temperature for 40 minutes. The reaction mixture was concentrated on a rotary evaporator and the crude HCl salt was taken up in anhydrous tetrahydrofuran (3 mL). To this solution was added N-succinimidyl 6-(2,4-dinitroanilino)hexanoate (0.288 g, 0.791 mmol) and triethylamine (102 mL, 0.731 mmol). The reaction mixture was stirred at room temperature for 30 minutes and the solvent was evaporated. The residue was partitioned between ethyl acetate and water and the phases were separated. The organic phase was washed with saturated NaHCO3 and saturated NaCl. It was dried over MgSO4, filtered, and concentrated under reduced pressure to yield the crude product (0.293 g) as a yellow oil. Purification using a Thomson Instruments Single Step 12 g silica gel cartridge eluting with 50% hexanes/50% ethyl acetate followed by ethyl acetate gave the product (0.222 g, 72%) as a yellow oil. 1H NMR (DMSO-d6) δ 1.32 (2H, m), 1.52-1.64 (4H, m), 2.15 (2H, t, J=7.0 Hz), 3.44 (2H, m), 3.59 (1H, m), 3.66 (1H, m), 4.33 (1H, m), 4.55 (2H, m), 5.02 (1H, t, J=5.5 Hz), 5.17 (1H, m), 5.28 (1H, m), 5.83 (1H, m), 7.21 (1H, d, J=9.5 Hz), 8.12 (1H, d, J=7.9 Hz), 8.23 (1H, dd, J=2.5 Hz, J=9.4 Hz), 8.85 (2H, m).

Workup

  1. concentrationThe reaction mixture was concentrated on a rotary evaporator
  2. customthe solvent was evaporated
  3. customThe residue was partitioned between ethyl acetate and water
  4. customthe phases were separated
  5. washThe organic phase was washed with saturated NaHCO3 and saturated NaCl
  6. dry with materialIt was dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto yield the crude product (0.293 g) as a yellow oil
  10. customPurification
  11. washeluting with 50% hexanes/50% ethyl acetate

Sources & evidence

ORD record
ord-115bc1857571409f9d09b097fe1fbc63
Source dataset
uspto-grants-2014_04
Patent number
US08703907B2

Reaction notes

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