3-Chlorophenol → HCID 71061709, compound

HRID 1524186Notes

Reaction equation

HRID 1524186 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.[Cl:20][C:21]1[CH:22]=[C:23](O)[CH:24]=[CH:25][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:20][C:21]1[CH:26]=[C:25]([CH:24]=[CH:23][CH:22]=1)[O:19][CH2:18][C@H:14]1[O:15][CH2:16][CH2:17][N:12]([CH2:11][CH2:10][N:1]2[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH2:3][CH2:2]2)[CH2:13]1

Participants

6

Reactant 4

HCID 79333-ChlorophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 71062870HCID 71062870, compound

Product 1

HCID 71061709HCID 71061709, compoundYield 40.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Compound 23s was synthesised with essentially the same procedure as compound 18s (Example 16), from compound 51 (Example 10; 52 mg, 0.2 mmol), 3-chlorophenol (39 mg, 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 (30 mg; 40%). 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-e74890c273b94605a027ba2627def92e
Source dataset
uspto-grants-2015_07
Patent number
US09079895B2

Reaction notes

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