Tetrahydrofuran → HCID 22137590, compound

HRID 1827338Notes

Reaction equation

HRID 1827338 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4](/[CH:7]=[CH:8]/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])[CH2:3][CH2:2]1.C1COCC1.C1C(=O)N([O:26][C:27]([O:29][CH2:30][CH:31]2[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]3[C:32]2=[CH:33][CH:34]=[CH:35][CH:36]=3)=O)C(=O)C1>C([O-])(O)=O.[Na+]>[CH:42]1[C:43]2[CH:31]([CH2:30][O:29][C:27]([N:1]3[CH2:6][CH2:5][CH:4](/[CH:7]=[CH:8]/[CH:9]=[CH:10]/[C:11]([OH:13])=[O:12])[CH2:3][CH2:2]3)=[O:26])[C:32]3[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:38]=2[CH:39]=[CH:40][CH:41]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimideHCID 22137601HCID 22137601, compound

Product 1

HCID 22137590HCID 22137590, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

The above solid (24) was taken up in saturated NaHCO3 (50 mL)/THF (50 mL). To this was added Fmoc-Osu (3.0 g, 9.0 mmol) at room temperature. The suspension became clear within 30 min. After stirring at room temperature overnight, the solution was concentrated to remove organic solvent, the resulting white suspension was acidified with 1 N HCl (50 mL) and extracted with EtOAc (3×100 mL). The combined organic extracts were dried (MgSO4) and concentrated to give a white solid (25) (3.63 g, >100%). 1H NMR (500 MHz, CDCL3) δ 7.77 (d, J=7.5 Hz, 2H), 7.58 (d, J=8.0 Hz, 2H), 7.40 (t, J=7.5 Hz, 2H), 7.34 (dd, J=15.0, 11.0 Hz, 1H), 7.32 (t, J=7.5 Hz, 2H), 6.21 (dd J=15.0, 11.0 Hz, 1H), 6.09 (dd, J=15.0, 7.0 Hz, 1H), 5.85 (d, J=15.5 Hz, 1H), 4.45 (br s, 2H), 4.18 (m, 3H), 2.83 (br s, 2H), 2.31 (m, 1H), 1.72 (m, 2H), 1.26 (m, 2H); MS (ES+) m/z 404.81 (M+H+).

Workup

  1. concentrationthe solution was concentrated
  2. customto remove organic solvent
  3. extractionextracted with EtOAc (3×100 mL)
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-d26415070bc0453c8de3c974c09df283
Source dataset
uspto-grants-2006_05
Patent number
US07053214B2

Reaction notes

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