Tetrahydrofuran → HCID 2756085, compound

HRID 1827339Notes

Reaction equation

HRID 1827339 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:4][CH:3]=1.C1C(=O)N([O:21][C:22]([O:24][CH2:25][CH:26]2[C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:32]3[C:27]2=[CH:28][CH:29]=[CH:30][CH:31]=3)=O)C(=O)C1.C1COCC1>C([O-])(O)=O.[Na+]>[CH:37]1[C:38]2[CH:26]([CH2:25][O:24][C:22]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=[O:12])=[CH:6][CH:7]=3)=[O:21])[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]=2[CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 270494-(4-Aminophenyl)butanoic acidHCID 134122N-(9-Fluorenylmethoxycarbonyloxy)succinimide

Product 1

HCID 2756085HCID 2756085, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a suspension of 4-(4-aminophenyl)butyric acid (3.0 g, 16.7 mmol) in 30 mL of saturated NaHCO3 was added Fmoc-Osu and 20 mL of THF. The mixture was stirred at room temperature overnight. After dilution with 1 N HCl, the product was extracted with ethyl acetate (3×100 mL). The combined extracts were washed with dilute HCl, brine, dried (Na2SO4) and concentrated to give a white solid 6.6 g (26) (98%). 1H NMR (500 MHz, CD3OD) δ 7.80 (m, 2H), 7.70 (m, 2H), 7.39 (m, 3H), 7.32 (m, 4H), 7.90 (m, 2H), 4.46 (m, 2H), 4.27 (t, J=7.0 Hz, 1H), 2.60 (t, J=8.0 Hz, 2H), 2.28 (t, J=7.0 Hz, 2H), 1.87 (m, 2H); MS (ESI+) m/z 424.19 (M+Na+).

Workup

  1. extractionAfter dilution with 1 N HCl, the product was extracted with ethyl acetate (3×100 mL)
  2. washThe combined extracts were washed with dilute HCl, brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-358f8daa644d4b249be669c56c3e37e1
Source dataset
uspto-grants-2006_05
Patent number
US07053214B2

Reaction notes

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