3-Methoxyphenol → HCID 71062708, compound

HRID 1524188Notes

Reaction equation

HRID 1524188 reaction equation
[N:1]1([CH2:10][CH2:11][N:12]2[CH2:17][CH2:16][O:15][C@H:14]([CH2:18][OH:19])[CH2:13]2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH2:2]1.[CH3:20][O:21][C:22]1[CH:23]=[C:24](O)[CH:25]=[CH:26][CH:27]=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:26]3[CH:25]=[CH:24][CH:23]=[C:22]([O:21][CH3:20])[CH:27]=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 90073-MethoxyphenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 71062870HCID 71062870, compound

Product 1

HCID 71062708HCID 71062708, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Essentially the same procedure was used to make compound 25s as was used for compound 18s (Example 16), with compound 51 (Example 10; 52 mg, 0.2 mmol), 3-methoxyphenol (0.032 ml, 0.3 mmol), triphenylphosphine (78 mg, 0.3 mmol), DEAD (0.05 ml, 0.3 mmol), and THF (1 ml). The crude residue was purified twice by flash column chromatography (silica, DCM/MeOH 1:0 to 8:2) to afford the title compound as a colourless oil (46 mg; 62%). Analyses were performed on the free base, and the free base was converted to the HCl salt for testing.

Workup

  1. customThe crude residue was purified twice by flash column chromatography (silica, DCM/MeOH 1:0 to 8:2)

Sources & evidence

ORD record
ord-f568548137664ba88bd0a9f9dc1cf40b
Source dataset
uspto-grants-2015_07
Patent number
US09079895B2

Reaction notes

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