Phenol → HCID 71062646, compound

HRID 1524184Notes

Reaction equation

HRID 1524184 reaction equation
[N:1]1([C:10](=O)[CH2:11][N:12]2[CH2:17][CH2:16][O:15][C@@H:14]([CH2:18][O:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22]N=3)[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[C:27]1(O)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[N:1]1([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][C@H:14]([CH2:18][O:19][C:20]3[CH:27]=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 996PhenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 71062807HCID 71062807, compound

Product 1

HCID 71062646HCID 71062646, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 19s was synthesised by essentially the same procedure as compound 18s (Example 16), using compound 51 (Example 12; 52 mg, 0.2 mmol), phenol (28 mg, 0.3 mmol), triphenylphosphine (78 mg, 0.3 mmol), DEAD (0.05 ml, 0.3 mmol), THF (1 ml). The crude residue was purified twice by flash chromatography to afford the title compound as a colourless oil (28 mg; 41%). Analyses were performed on the free base, and it was converted to the HCl salt for testing.

Workup

  1. customThe crude residue was purified twice by flash chromatography

Sources & evidence

ORD record
ord-2ce64d8f502d46e0b1dae75cafb8424e
Source dataset
uspto-grants-2015_07
Patent number
US09079895B2

Reaction notes

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