Formic Acid → HCID 22185903, compound

HRID 252307Notes

Reaction equation

HRID 252307 reaction equation
C([O:4][C:5](=[O:28])[CH2:6][C:7]1([CH2:13][NH:14][C:15]([O:17][CH:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:20](=[O:27])[O:19]2)=[O:16])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)C=C.C(O)=O>O1CCCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[O:27]=[C:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]([O:17][C:15]([NH:14][CH2:13][C:7]2([CH2:6][C:5]([OH:28])=[O:4])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[O:16])[O:19]1

Participants

5

Reactant 2

HCID 284Formic AcidHCID 86590567HCID 86590567, compound

Product 1

HCID 22185903HCID 22185903, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (55) (0.12 g, 0.31 mmol) in dry tetrahydrofuran was added tetrakis(triphenylphosphine)-palladium(0) (5.5 mg, 4.8×10−3 mmol) and formic acid (57 mg, 1.24 mmol). The resulting reaction was stirred at room temperature for 12 h (monitored by LC/MS), then filtered through a Celite® and activated charcoal pad. The pad was washed with ethyl acetate (2×15 mL) and the combined filtrates were washed with brine (20 mL), dried over MgSO4 and concentrated in vacuo. The resulting residue was purified using preparative-LC/MS to provide 80 mg of compound (53) as a white solid (74% yield). 1H NMR (400 MHz, CDCl3) δ 1.35-1.58 (10H, m); 2.34 (2H, s); 3.23-3.40 (2H, m); 5.56 (1H, t, J=7.2 Hz); 7.42 (1H, s); 7.60-7.66 (2H, dd, J=7.6 Hz); 7.74 (1H, t, J=7.6 Hz); 7.91 (1H, d, J=7.6 Hz). MS (ESI): m/z=346.40 (M+H+).

Workup

  1. customThe resulting reaction
  2. filtrationfiltered through a Celite® and activated charcoal pad
  3. washThe pad was washed with ethyl acetate (2×15 mL)
  4. washthe combined filtrates were washed with brine (20 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified

Sources & evidence

ORD record
ord-4c3714b6af5541f5b4feb2ddfac10490
Source dataset
uspto-grants-2011_01
Patent number
US07868041B2

Reaction notes

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