Allyl Alcohol → HCID 21075408, compound

HRID 1373749Notes

Reaction equation

HRID 1373749 reaction equation
[CH2:1]([O:4][C:5]1[N:10]=[C:9]([NH:11][C:12]([NH:14][C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[OH:22])=[O:13])[CH:8]=[N:7][C:6]=1[C:23]#[N:24])[CH:2]=[CH2:3].[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:30]=CC=C[CH:26]=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O.C(O)C=C>O1CCCC1>[CH2:30]([O:22][C:16]1[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=1[NH:14][C:12]([NH:11][C:9]1[CH:8]=[N:7][C:6]([C:23]#[N:24])=[C:5]([O:4][CH2:1][CH:2]=[CH2:3])[N:10]=1)=[O:13])[CH:25]=[CH2:26]

Participants

6

Reactant 4

HCID 7858Allyl AlcoholHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 135848698HCID 135848698, compound

Product 1

HCID 21075408HCID 21075408, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Example 55A (456 mg, 1.32 mmol) in anhydrous tetrahydrofuran (18 mL) was added polymer supported triphenylphosphine (659.5 mg, 1.98 mmol), di-tert-butyl azodicarboxylate (455.5 mg, 1.98 mmol), and allyl alcohol (76.6 mg, 1.32 mmol). The reaction mixture was shaken at room temperature for 5 hours. The solution was filtered, dried with silica gel powder (10 g), and purified by flash chromatography eluting with 20% ethyl acetate in hexanes (2 L) to give the title compound (140.8 mg, 28%). MS (ESI) m/z 385.95 (M+H)+; 1H NMR (500 MHz, DMSO-D6) δ ppm 4.71 (d, J=5.62 Hz, 2 H) 4.95 (d, J=5.30 Hz, 2 H) 5.29–5.36 (m, 2 H) 5.40–5.48 (m, 2 H) 6.00–6.16 (m, 2 H) 7.04–7.10 (m, 2 H) 8.20 (d, J=2.50 Hz, 1 H) 8.88 (s, 1 H) 9.05 (s, 1 H) 10.71 (s, 1 H).

Workup

  1. filtrationThe solution was filtered
  2. customdried with silica gel powder (10 g)
  3. custompurified by flash chromatography
  4. washeluting with 20% ethyl acetate in hexanes (2 L)

Sources & evidence

ORD record
ord-fcf2179861804f6085d8233ed81638c1
Source dataset
uspto-grants-2007_01
Patent number
US07163939B2

Reaction notes

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