Diisopropylethylamine → 17-(3-{Tert-butoxycarbonyl[2-(2,5-dioxopyrrolidin-1-yloxycarbonyl)ethyl]amino}propionylamino)heptadecanoic acid tert-butyl ester

HRID 2369797Notes

Reaction equation

HRID 2369797 reaction equation
[C:1]([O:5][C:6](=[O:41])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:40])[CH2:25][CH2:26][N:27]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.[B-](F)(F)(F)F.CN(C(O[N:64]1[C:69](=[O:70])[CH2:68][CH2:67][C:65]1=[O:66])=[N+](C)C)C>C1COCC1>[C:1]([O:5][C:6](=[O:41])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:40])[CH2:25][CH2:26][N:27]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:28][CH2:29][C:30]([O:32][N:64]1[C:69](=[O:70])[CH2:68][CH2:67][C:65]1=[O:66])=[O:31])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 8664713017-{3-[tert-Butoxycarbonyl (2-carboxyethyl)amino]propionylamino}heptadecanoic acid tert-butyl ester

Product 1

HCID 8756539517-(3-{Tert-butoxycarbonyl[2-(2,5-dioxopyrrolidin-1-yloxycarbonyl)ethyl]amino}propionylamino)heptadecanoic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

17-{3-[tert-Butoxycarbonyl (2-carboxyethyl)amino]propionylamino}heptadecanoic acid tert-butyl ester (0.122 g, 0.2 mmol) was dissolved in THF (5 mL). DIEA (39 ul) was added and the mixture was cooled to 0° C. TSTU (66 mg, 0.22 mmol) was added. The mixture was stirred at 0° C. for 30 min, then for 16 h at RT. The mixture was concentrated under vacuum. AcOEt (15 mL) and the solution was washed with 0.2 N HCl (5 ml) and sat. NaCl (5 ml), dried over MgSO4, and dried under vacuum. The residue was purified by flash chromatography (silica) eluting with AcOEt/heptane (9:1) and AcOEt. The appropriate fractiones were pooled and concentrated under vacuum to yield 58 mg.

Workup

  1. waitfor 16 h at RT
  2. concentrationThe mixture was concentrated under vacuum
  3. washAcOEt (15 mL) and the solution was washed with 0.2 N HCl (5 ml) and sat. NaCl (5 ml)
  4. dry with materialdried over MgSO4
  5. customdried under vacuum
  6. customThe residue was purified by flash chromatography (silica)
  7. washeluting with AcOEt/heptane (9:1) and AcOEt
  8. concentrationconcentrated under vacuum
  9. customto yield 58 mg

Sources & evidence

ORD record
ord-2f8a6949ee444f68835671292bda2f1c
Source dataset
uspto-grants-2014_04
Patent number
US08710000B2

Reaction notes

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